- GaCl3-catalyzed activation of alkynyl glycosides for the synthesis of O-glycosides
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A catalytic amount of GaCl3 (5 mol%) was found to activate alkynyl glycosides effectively under mild reaction conditions to furnish a variety of O-glycosides in good yields with high β-selectivity. Graphical abstract: [Figure not available: see fulltext.]
- Yadav, Jhillu S.,Yadav, Nagendra N.,Gupta, Manoj K.,Srivastava, Nikhil,Subba Reddy, Basi V.
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- Synthesis of photolabile group protected anomeric acetals and its application in carbohydrate synthesis with the assistance of continuous flow photo-reactor
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Selective deprotection of photolabile anomeric 2-nitrobenzyl acetals was achieved using continuous flow photo-reactor (UV radiation at 355 nm) in methanol-water. Various protecting groups such as acetyl, benzyl, benzoyl, benzylidine, TBS, etc. were found to be highly stable during the photolysis.
- Tiwari, Varsha,Badavath, Vishnu Nayak,Singh, Adesh Kumar,Kandasamy, Jeyakumar
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p. 227 - 236
(2020/03/18)
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- New class of alkynyl glycoside analogues as tyrosinase inhibitors
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A new series of alkynyl glycoside analogues were designed and synthesized from cheap and a commercially available sugar by introduction of various alkynyl and alkyl groups at C-1 and C-6 positions of the sugar ring. The inhibitory abilities of alkynyl gly
- Saehlim, Natthiya,Athipornchai, Anan,Sirion, Uthaiwan,Saeeng, Rungnapha
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supporting information
(2020/06/01)
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- Direct dehydrative glycosylation catalyzed by diphenylammonium triflate
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Methods for direct dehydrative glycosylations of carbohydrate hemiacetals catalyzed by diphenylammonium triflate under microwave irradiation are described. Both armed and disarmed glycosyl-C1-hemiacetal donors were efficiently glycosylated in moderate to excellent yields without the need for any drying agents and stoichiometric additives. This method has been successfully applied to a solid-phase glycosylation.
- Hsu, Mei-Yuan,Lam, Sarah,Lin, Mei-Huei,Lin, Su-Ching,Wang, Cheng-Chung,Wu, Chia-Hui
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supporting information
(2020/03/13)
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- An Unexpected FeCl 3/C-Catalyzed β-Stereoselective Glycosylation in the Presence of the C(2)-Benzyl Group
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An efficient and completely β-stereoselective glycosylation that did not rely on neighboring group participation is described using 2-20 molpercent FeCl 3 /C as the catalyst and benzylated propargyl glycosides as the donors to reach yields up to 96percent under mild condition. With an octatomic-ring intermediate at the α-face of FeCl 3 /C with alkyne of propargyl glycosides, a panel of aglycones comprising aliphatic, alicyclic, unsaturated alcohols, halogenated alcohols, and phenols with different substitution were examined successfully for the exclusive β-stereoselective glycosylation reaction.
- Guo, Hong,Li, Juan,Si, Wenshuai,Tang, Jie,Tang, Tianjun,Wang, Zhongfu,Yang, Guofang,Zhang, Jianbo
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p. 2984 - 3000
(2019/07/22)
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- N-benzoylglycine/thiourea cooperative catalyzed stereoselective O-glycosidation: Activation of O-glycosyl trichloroacetimidate donors
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A new practical utility for β-stereoselective glycosylation via activation of O-glycosyl trichloroacetimidate donors using N-benzoylglycine/thiourea cooperative catalysis has been demonstrated. This method represents the first instance where amino acid derived N-benzoylglycine is used as a catalyst for O–glycosylation under mild reaction conditions at ambient temperature. NMR spectroscopy studies suggest that thiourea cocatalyst exhibit a cooperative behaviour that has a strong effect on the reaction rate, yield, and the β-selectivity.
- Dubey, Atul,Sangwan, Rekha,Mandal, Pintu Kumar
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p. 123 - 129
(2019/04/17)
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- β-Selective Glycosylation by Using O-Aryl-Protected Glycosyl Donors
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New glycosyl donors have been developed that contained several para-substituted O-aryl protecting groups and their stereoselectivity for the glycosylation reaction was evaluated. A highly β-selective glycosylation reaction was achieved by using thioglycosides that were protected by 4-nitrophenyl (NP) groups, which were introduced by using the corresponding diaryliodonium triflate. Analysis of the stereoselectivities of several glycosyl donors indicated that the β-glycosides were obtained through an SN2-type displacement from the corresponding α-glycosyl triflate. The NP group could be removed by reduction of the nitro group and acylation, followed by oxidation with ceric ammonium nitrate (CAN).
- Otsuka, Yuji,Yamamoto, Toshihiro,Fukase, Koichi
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supporting information
p. 2719 - 2723
(2019/07/15)
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- Visible Light Enables Aerobic Iodine Catalyzed Glycosylation
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A versatile protocol for light induced catalytic activation of thioglycosides using iodine as an inexpensive and readily available photocatalyst was developed. Oxygen serves as a green and cost-efficient terminal oxidant and irradiation is performed with a common household LED-bulb. The scope of this glycosylation protocol was investigated in the synthesis of O-glycosides with yields up to 95 %.
- Krumb, Matthias,Lucas, Tobias,Opatz, Till
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supporting information
p. 4517 - 4521
(2019/08/06)
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- Silver-catalyzed stereoselective formation of glycosides using glycosyl ynenoates as donors
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A silver-catalyzed glycosylation reaction employing readily accessible and stable glycosyl ynenoates is developed. This reaction is mostly high yielding and exhibits varying levels of stereoinversion at the anomeric position. Compared to established and versatile Yu's gold catalysis, this chemistry features the use of substantially cheaper AgNTf2.
- Dong, Xu,Chen, Li,Zheng, Zhitong,Ma, Xu,Luo, Zaigang,Zhang, Liming
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p. 8626 - 8629
(2018/08/06)
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- Efficient Synthesis of α-Glycosyl Chlorides Using 2-Chloro-1,3-dimethylimidazolinium Chloride: A Convenient Protocol for Quick One-Pot Glycosylation
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A mild and convenient method for the synthesis of α-glycosyl chlorides in high 80–96 % yields within 15–30 min using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) is disclosed. The method has a wide substrate scope and is compatible with labile OH protecting groups, including benzyl, acetyl, benzoyl, isopropylidene, benzylidene, TBDMS (tert-butyldimethylsilyl), and TBDPS (tert-butyldiphenylsilyl) groups. The excellent α selectivity obtained in this reaction is attributed to in-situ isomerization of β-glycosyl chlorides to the more stable α-glycosyl chlorides, as demonstrated by 1H NMR spectroscopic studies. Disarmed sugars with OBz or OAc groups at C-2 were chlorinated at a faster rate but ismomerized (β→α) at a slower rate than armed sugars with an OBn group at C-2. More importantly, the method enables highly desirable one-pot glycosylation reactions to take place, thus allowing efficient syntheses of disaccharides and simple O-glycosylated sugars in high overall yields without the need for separation or purification of the α-glycosyl chloride donors. This method will be especially useful for direct glycosylation reactions using glycosyl chloride donors that are unstable upon separation and purification.
- Tatina, Madhu Babu,Khong, Duc Thinh,Judeh, Zaher M. A.
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supporting information
p. 2208 - 2213
(2018/06/04)
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- Tris(pentafluorophenyl)borane-promoted stereoselective glycosylation with glycosyl trichloroacetimidates under mild conditions
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Tris(pentafluorophenyl)borane-promoted stereoselective glycosylation with trichloroacetimidate glycosyl donors is described. The reactions proceed efficiently with a wide range of acceptors, from sugar to nonsugar, under mild conditions in the presence of
- Mishra, Kunj Bihari,Singh, Adesh Kumar,Kandasamy, Jeyakumar
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p. 4204 - 4212
(2018/04/14)
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- Electron-deficient pyridinium salts/thiourea cooperative catalyzed O-glycosylation via activation of O-glycosyl trichloroacetimidate donors
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The glycosylation of O-glycosyl trichloroacetimidate donors using a synergistic catalytic system of electron-deficient pyridinium salts/aryl thiourea derivatives at room temperature is demonstrated. The acidity of the adduct formed by the 1, 2-addition of
- Shaw, Mukta,Kumar, Yogesh,Thakur, Rima,Kumar, Amit
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supporting information
p. 2385 - 2395
(2017/11/16)
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- Metal-free and VOC-free: O -glycosylation in supercritical CO2
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Supercritical carbon dioxide (scCO2) is a suitable medium to perform transition metal-free glycosylation reactions in the absence of volatile organic solvents (VOCs) using glycosyl halides as glycosyl donors. The methodology described here can be applied for obtaining O-glycosides in a totally green reaction, as well as orthoesters, depending on the reaction conditions. The process is much more sensitive to temperature changes than to pressure modification, with glycosyl chlorides requiring higher temperatures to be activated than glycosyl bromides. Pivaloyl groups act as good CO2-philic units and are shown to be the best choice to obtain good stereoselectivities. The relevance of the fluid nature and supercritical conditions was also evidenced.
- Cardona, Adrià,Boutureira, Omar,Castillón, Sergio,Díaz, Yolanda,Matheu, M. Isabel
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supporting information
p. 2687 - 2694
(2017/07/17)
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- Dehydrative glycosylation with cyclic phosphonium anhydrides
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Cyclic phosphonium anhydrides generated from bis-phosphine oxides and trifluoromethanesulfonic anhydride are shown as general coupling reagents in a dehydrative glycosylation reaction of C1-hemiacetals. This reaction protocol is characterized by a broad substrate scope and high yields, including reactions of O-, C-, N-, and S-based nucleophiles with furanose, pyranose, and deoxysugar donors.
- Dyapa, Rajendar,Dockery, Lance T.,Walczak, Maciej A.
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supporting information
p. 51 - 55
(2016/12/27)
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- A 1,2-trans-Selective Glycosyl Donor Bearing Cyclic Protection at the C-2 and C-3 Hydroxy Groups
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A new 1,2-trans-selective glycosylation reaction is described. Glucosyl donors protected cyclically at the C-2 and C-3 hydroxy groups as six- (butane diacetal), seven- (tetraisopropyldisiloxanylidene), or eight- (2,3-o-xylylene) membered fused rings were synthesized in a straightforward manner. The glycosylation reactions of the glucosyl donors with various acceptors mainly generated β-glycosides under conventional reaction conditions. The results show that the o-xylylene group is a suitable 1,2-trans-directing group from the points of view of stereoselectivity and chemical stability. A conformational study of the oxocarbenium ion of an o-xylylene-protected glucose derivative by NMR spectroscopy and computational simulation was carried out. The results imply that the oxocarbenium ion mainly adopts a 4H3 conformation owing to the rigid trans-fused ring at C-2 and C-3, while a noncyclically protected derivative might fluctuate between conformations. These results suggest that an eclipsing interaction between the pseudoequatorial xyloxy group at C-2 and the incoming nucleophile hampers 1,2-cis attack.
- Yagami, Nahoko,Tamai, Hideki,Udagawa, Taro,Ueki, Akiharu,Konishi, Miku,Imamura, Akihiro,Ishida, Hideharu,Kiso, Makoto,Ando, Hiromune
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supporting information
p. 4778 - 4785
(2017/09/07)
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- A versatile glycosylation strategy: Via Au(III) catalyzed activation of thioglycoside donors
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Among various methods of chemical glycosylations, glycosylation by activation of thioglycoside donors using a thiophilic promoter is an important strategy. Many promoters have been developed for the activation of thioglycosides. However, incompatibility w
- Vibhute, Amol M.,Dhaka, Arun,Athiyarath, Vignesh,Sureshan, Kana M.
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p. 4259 - 4263
(2016/07/06)
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- A novel selectfluor-mediated regioselective O-benzyl ether acetolysis of perbenzylated monosaccharides
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Selectfluor, a source of the super electrophile F+, has replaced conventional reagents that supply F+ for fluorination due to its attractive physical and chemical properties. This study is the first report of using Selectfluor as a d
- Tambie, Marlon S.,Jalsa, Nigel Kevin
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p. 545 - 559
(2016/04/19)
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- Gold-catalysed glycosylation reaction using an easily accessible leaving group
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Gold(iii)-catalysed glycosylation reaction has been developed by employing a new and easily accessible leaving group synthesized from ethyl cyanoacetate. Several nucleophiles like alcohols, thiols, allyltrimethylsilane, trimethylsilyl azide and triethylsilane have been reacted to make the corresponding glycosides in good yields and with marginal to excellent α-selectivity. This journal is
- Koppolu, Srinivasa Rao,Niddana, Ramana,Balamurugan, Rengarajan
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p. 5094 - 5097
(2015/05/13)
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- Strained olefin enables triflic anhydride mediated direct dehydrative glycosylation
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For the first time, we demonstrated that Tf2O mediated direct dehydrative glycosylation was possible simply with strained olefins, and other typical bases were inhibitors of this reaction. We optimized the glycosylation conditions and found tha
- Chen, Guohua,Yin, Qiang,Yin, Jian,Gu, Xiangying,Liu, Xiao,You, Qidong,Chen, Yue-Lei,Xiong, Bing,Shen, Jingkang
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supporting information
p. 9781 - 9785
(2015/01/08)
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- Gold(III) Chloride and Phenylacetylene: A Catalyst System for the Ferrier Rearrangement, and O-Glycosylation of 1-O-Acetyl Sugars as Glycosyl Donors
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We have developed a new catalyst system comprising AuCl3 and phenylacetylene that promotes the Ferrier rearrangement of glycals and 2-acetoxymethylglycals with different nucleophiles, and also the O-glycosylation of 1-O-acetyl sugars to obtain a variety of useful glycosides at room temperature through relay catalysis. Good anomeric selectivity was observed for the Ferrier rearrangements, whereas the O-glycosylation of 1-O-acetyl sugars gave mixtures of diastereomers with moderate to excellent selectivity.
- Roy, Rashmi,Rajasekaran, Parasuraman,Mallick, Asadulla,Vankar, Yashwant D.
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p. 5564 - 5573
(2014/10/15)
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- Direct glycosylation of bioactive small molecules with glycosyl iodide and strained olefin as acid scavenger
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A new strategy for diversity-oriented direct glycosylation of bioactive small molecules was developed. This reaction features (-)-β-pinene as acid scavenger and work with glycosyl iodides under mild conditions. With the aid of RP-HPLC and chiral SFC separation techniques, the new direct glycosylation proved effective at gram scale on bioactive small molecules including AZD6244, podophyllotoxin, paclitaxel, and docetaxel. Interesting glycoside derivatives were efficiently created with good yields and 1,2-cis selectivity.
- Gu, Xiangying,Chen, Lin,Wang, Xin,Liu, Xiao,You, Qidong,Xi, Wenwei,Gao, Li,Chen, Guohua,Chen, Yue-Lei,Xiong, Bing,Shen, Jingkang
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p. 1100 - 1110
(2014/03/21)
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- Cooperative catalysis in glycosidation reactions with o-glycosyl trichloroacetimidates as glycosyl donors
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Thiourea mediates cooperative glycosidation through hydrogen bonding. N,N′-Diarylthiourea as cocatalyst enforces an SN2-type acid-catalyzed glycosidation even at room temperature (see scheme; Bn=benzyl). From O-(α-glycosyl) trichloroacetimidates as glycosyl donors and various acceptors, β-glycosides are preferentially or exclusively obtained.
- Geng, Yiqun,Kumar, Amit,Faidallah, Hassan M.,Albar, Hassan A.,Mhkalid, Ibrahim A.,Schmidt, Richard R.
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supporting information
p. 10089 - 10092
(2013/10/01)
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- GLYCOSYLATED VALPROIC ACID ANALOGS AND USES THEREOF
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Glycosylated valproic acid and its analogs are provided. In some embodiments, the glycosylated valproic acid and its analogs have improved solubility and are ideal for drug delivery to treat a variety of diseases.
- -
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Paragraph 0230; 0231
(2013/03/26)
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- Synthesis of multivalent glucosides with high affinity for GLUT1 transporter
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The novel bifunctional compounds L1 and L2 carrying cluster glucosides as ligands for brain targeting liposomes were synthesized. 2-phenyl-1,3-dioxan-5-ol (8) and tetra-antennary alcohol (13) were used as the core scaffold to attach cholesterol derivatives by a triethylene glycol chain, while their remaining branches were linked with two or three benzylglucosides, which would be debenzvlated later to produce di-antennary glucosides L1 and tri-antennary glucosides ligand L2. This design provided an effective entry for the synthesized bifunctional compounds to cross blood brain barrier (BBB).
- Qu, Boyi,Li, Xun,Wu, Jianbo,Li, Xiaolong,Hai, Li,Wu, Yong
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scheme or table
p. 390 - 395
(2012/08/29)
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- Using In(III) as a promoter for glycosylation
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InCl3, InBr3, and In(OTf)3 were tested as promoters in the preparation of glycosides from trichloroacetimidate precursors. A range of protecting groups and of alcohol acceptors were used to determine the versatility of these promoters. Disaccharide formation was demonstrated. In most cases, the In(III) compounds were shown to promote glycosylation better than the widely used promoter BF3·OEt2.
- Mattson, Amanda L.,Michel, Anna K.,Cloninger, Mary J.
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scheme or table
p. 142 - 146
(2012/03/10)
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- Glycosylation using unprotected alkynyl donors
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(Chemical Equation Presented) Gold(III) activation of unprotected propargyl glycosyl donors has been shown to be effective for the synthesis of saccharides. Terminal propargyl glycosides of glucose, galactose, and mannose required heating at reflux in ace
- Mamidyala, Sreeman K.,Finn
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experimental part
p. 8417 - 8420
(2010/01/16)
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- [bmim][OTf]: a versatile room temperature glycosylation promoter
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[bmim][OTf] is a versatile, ionic liquid promoter for the room temperature glycosylation of both thiophenyl and trichloroacetimidate glycoside donors; the conditions are mild, with no requirement for molecular sieves, and are compatible with a wide range
- Galan, M. Carmen,Brunet, Claire,Fuensanta, Monica
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supporting information; body text
p. 442 - 445
(2009/05/27)
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- Stereoselective synthesis of branched cyclopentitols by titanium(III)-promoted reductive cyclization of 4-oxiranylaldehydes and 4-oxiranyl ketones derived from hexoses
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Titanocene chloride efficiently promotes the intramolecular reductive cross coupling of highly functionalized 4-oxiranyl-aldehydes and 4-oxiranyl ketones derived from readily available hexoses affording branched cyclopentitols with good stereoselectivity.
- Chiara, Jose Luis,Bobo, Sofia,Sesmilo, Esther
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scheme or table
p. 3160 - 3166
(2009/04/06)
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- Propargyl glycosides as stable glycosyl donors: Anomeric activation and glycoside syntheses
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The advantages of stable glycosyl donors for saccharide coupling are many, and we describe herein the utility of propargyl glycosides for anomeric activation and glycoside synthesis exploiting the alkynophilicity of AuCl3. Various aglycones wer
- Hotha, Srinivas,Kashyap, Sudhir
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p. 9620 - 9621
(2007/10/03)
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- Glycosyl trichloroacetylcarbamate: A new glycosyl donor for O-glycosylation
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Glycosyl trichloroacetylcarbamates, readily obtained by reacting 1-hydroxy sugars with trichloroacetylisocyanate, have been found as excellent glycosyl donors, and the corresponding O-glycosides are formed in good to excellent yields with a fairly good degree of selectivity.
- Jayakanthan,Vankar, Yashwant D.
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p. 2688 - 2692
(2007/10/03)
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- An expedient synthesis of benzyl 2,3,4-tri-O-benzyl-β-D- glucopyranoside and benzyl 2,3,4-tri-O-benzyl-β-D-mannopyranoside
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An efficient three-step synthesis of benzyl 2,3,4-tri-O-benzyl-β-d- glucopyranoside, a widely used building block in carbohydrate chemistry, is described. The key step is the selective debenzylation-acetylation of perbenzylated β-glucose using ZnCl2
- Lu, Wallach,Navidpour, Latifeh,Taylor, Scott D.
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p. 1213 - 1217
(2007/10/03)
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- Stereoselective and effective synthesis of alkyl α-D-gluco- and α-D-galactopyranosides
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Practical, improved synthesis of alkyl α-D-glycopyranosides by reaction of O-gluco- or O-galactopyranosyl N-allyl thiocarbamate with bromine followed by addition of alcohol is described. This process proceeded very fast to give the glycosides in good yiel
- Kasprzycka,Szeja
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p. 329 - 333
(2007/10/03)
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- Catalytic glycosylation with rhodium(III)-triphos catalysts
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The formation of glycosides in high yield from 1-hydroxy sugars using catalytic amounts (0.5molpercent) of Rh(III)Cl3(triphos) (1a) or [Rh(III)(MeCN)3(triphos)](TfO)3 (1b) is described. High stereocontrol at the anomeric c
- Wagner, Beatrice,Heneghan, Michael,Schnabel, Gerhard,Ernst, Beat
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p. 1303 - 1306
(2007/10/03)
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- Carbohydrates dithiocarbonic acid esters and their application in glycosylation reactions
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Allyl dithiocarbonic acid esters are used as efficient glycosyl donors in the presence of soft activators. Different glycosides are obtained in good yields, isomer α being the main product.
- Slusarczyk,Sieron,Szeja
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- Synthesis of monosaccharide-fused azetidines
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Primary amines reacted upon 4,6-ditosylates of glucopyranosides to give an azetidine ring fused on C-4 and C-6 of the pyranose ring. On the other hand, the 4,6-ditosylate of benzyl mannopyranoside led to the 4,6-diamino-4,6-dideoxy derivative in a good yield. All the compounds and their precursors were identified by 1H and 13C NMR spectroscopy. Assignments of proton signals were made unambiguously using homodecoupling experiments.
- Michaud, Thierry,Chanet-Ray, Josette,Chou, Sithan,Gelas, Jacques
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p. 253 - 269
(2007/10/03)
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- STUDIES ON GLYCOSIDES VI FACILE SYNTHESIS OF ALKYL α- AND β-D-GLUCOPYRANOSIDES
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A facile method for the synthesis of alkyl α- abd β-D-glucopyranosides using 1-O-trimethylsilyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose by the promotion of BF3Et2O was reported.The mixture of α- and β-anomers, in which β-anomers predominated, was obtained in good yields.
- Qui, Dong-Xu,Wang, Yan-Feng,Cai, Meng-Shen
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p. 3453 - 3456
(2007/10/02)
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- The Stereoselective Dehydrative α-Glucosylation Using 6-O-Acetyl- and 6-O-p-Nitrobenzoyl-2,3,4-tri-O-benzyl-D-glucopyranoses
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The stereoselective synthesis of α-linked glucobiose derivatives using 6-O-acetyl- or 6-O-p-nitrobenzoyl-2,3,4-tri-O-benzyl-D-glucopyranose and a ternary mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine in dichloromethane is described.
- Koto, Shinkiti,Morishima, Naohiko,Kihara, Yasuhiro,Suzuki, Hideko,Kosugi, Shigeharu,Zen, Shonosuke
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p. 188 - 191
(2007/10/02)
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- SYNTHESIS AND THREE-DIMENSIONAL STRUCTURES OF 3-(α-AMINO- and α-HYDROXYBENZYL)QUINUCLIDINES
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3-Substituted quinuclidines that contain a hydroxy or amino group in the side chain were synthesized by reduction of 3-benzoyl- and 3-benzoylmethylquinuclidines and their oximes.It is shown that the reduction of the ketones takes place stereospecifically
- Vorob'eva, V. Ya.,Mikhlina, E. E.,Turchin, K. F.,Sheinker, Yu. N.,Yakhontov, L. N.
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p. 310 - 314
(2007/10/02)
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- Stereoselective α-Glucosylation with Tetra-O-benzyl-α-D-glucose and a Mixture of Trimethylsilyl Bromide, Cobalt(II) Bromide, Tetrabutylammonium Bromide, and a Molecular Sieve. A Synthesis of 3,6-Di-O-(α-D-glucopyranosyl)-D-glucose
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A mixture of trimethylsilyl bromide, cobalt(II) bromide, tetrabutylammonium bromide, and a molecular sieve (4A) is effective for the stereoselective, one-stage α-glucosylation of alcohol with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose in dichloromethane.Using this procedure, several disaccharide derivatives as well as O-α-D-glucopyranosyl-(1 -> 3)-O- 6)>-D-glucopyranose are synthesized.
- Koto, Shinkiti,Morishima, Naohiko,Kusuhara, Chiharu,Sekido, Shigeko,Yoshida, Toyosaku,Zen, Shonosuke
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p. 2995 - 2999
(2007/10/02)
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- A Study of the Rapid Anomerization of Poly-O-benzyl-β-D-glucopyranosides with Titanium Tetrachloride
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Titanium tetrachloride rapidly anomerizes methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside in dichloromethane at 25 deg C.Evidence for the proposal that the benzyloxymethyl group on C-5 and the ring oxygen of the glucoside cooperate to prompt the reaction is described.The reagent anomerizes the interglycosidic linkage of several disaccharide derivatives.
- Koto, Shinkiti,Morishima, Naohiko,Kawahara, Reiko,Ishikawa, Katsuhiko,Zen, Shonosuke
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p. 1092 - 1096
(2007/10/02)
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