- Nδ-(5-Hydroxy-4,6-dimethylpyrimidine-2-yl)-L-ornithine, a novel methylglyoxal - Arginine modification in beer
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Nδ-(5-Hydroxy-4,6-dimethylpyrimidine-2-yl)-L-ornithine, or Argpyrimidine, was identified and quantified in beer by high-performance liquid chromatography (HPLC) and coupled gas chromatography-mass spectrometry (HRGC-MS). This novel fluorescent
- Glomb, Marcus A.,Roesch, Daniel,Nagaraj, Ramanakoppa H.
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- A three-acetyl deoxyribose α isomer preparation method
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The invention discloses a capecitabine intermediate impurity tri acetyl deoxyribose α isomer: the chemical name is 1 α - 1, 2, 3 - three-acetoxy - 5 - deoxy - D - ribose of the preparation method. The preparation method in order to 5 - deoxy - D - ribose as a synthetic raw material, by isopropenyl acetate/iron trichloride acetylation than three acetyl deoxyribose α isomer crude, passes through the column again chromatography purification to obtain the triacetyl deoxyribose α isomer pure product. The invention provides a triacetyl deoxyribose α isomer preparation method, with simple operation, the advantage of the high product purity, for capecitabine intermediate and the quality of the finished good foundation for the study.
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Paragraph 0013; 0014
(2019/07/04)
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- Synthesis of Nucleosides through Direct Glycosylation of Nucleobases with 5-O-Monoprotected or 5-Modified Ribose: Improved Protocol, Scope, and Mechanism
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Simplifying access to synthetic nucleosides is of interest due to their widespread use as biochemical or anticancer and antiviral agents. Herein, a direct stereoselective method to access an expansive range of both natural and synthetic nucleosides up to a gram scale, through direct glycosylation of nucleobases with 5-O-tritylribose and other C5-modified ribose derivatives, is discussed in detail. The reaction proceeds through nucleophilic epoxide ring opening of an in situ formed 1,2-anhydrosugar (termed “anhydrose”) under modified Mitsunobu reaction conditions. The scope of the reaction in the synthesis of diverse nucleosides and other 1-substituted riboside derivatives is described. In addition, a mechanistic insight into the formation of this key glycosyl donor intermediate is provided.
- Downey, A. Michael,Pohl, Radek,Roithová, Jana,Hocek, Michal
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p. 3910 - 3917
(2017/03/27)
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- NOVEL PROCESS FOR THE RECOVERY OF BETA ACETYLFURANOSIDE
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There is provided an improved method for the recovery of residual, unseparated β-ACF from reaction mixtures remaining from an initial synthesis of ACF, which is in particular usable on a large industrial scale, more particularly in the production of capecitabine.
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Page/Page column 3
(2010/08/07)
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- HYDROXAMIC ACID DERIVATIVES
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The disclosure includes hydroxamic compounds of Formula I: (I) wherein P, Z, and m are defined herein. Also disclosed is a method for treating a neoplastic disease or an immune disease with these compounds.
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- PREPARATION OF CAPECITABINE
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The present invention relates to substantially pure capecitabine and processes for the preparation thereof.
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Page/Page column 21; 22; 23
(2010/06/20)
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- METHOD FOR THE PREPARATION OF CAPECITABINE AND INTERMEDIATES USED IN SAID METHOD
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A process to obtain capecitabine compound and its pharmaceutically acceptable derivatives is hereby disclosed. Likewise, novel intermediates to be used in the preparation of capecitabine compound and its pharmaceutically acceptable derivatives are also disclosed. The procedure comprises the stage of causing a reaction of N4-(n-pentyloxycarbonyl))-5- fluorocytosine with (1,2,3-tri-O-acetyl-5-deoxy- α,β-D-ribofuranose.
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Page/Page column 8-9
(2010/11/03)
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- METHODS FOR PREPARING CAPECITABINE AND BETA-ANOMER-RICH TRIALKYL CARBONATE COMPOUND USED THEREIN
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The present invention relates to a method for preparing capecitabine and a method for preparing a β-anomer-rich trialkyl carbonate compound used therein, and a highly pure capecitabine can be efficiently prepared with a high yield by the method of the present invention using the β-anomer-rich trialkyl carbonate compound as an intermediate.
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Page/Page column 11
(2009/06/27)
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- METHOD FOR STEREOSELECTIVE PREPARATION AND SEPARATION OF TRI-O-ACETYL-5-DEOXY-β-D-RIBOFURANOSE
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The present invention discloses a method for preparing highly pure tri-O-acetyl-5-deoxy-β-D-ribofuranose which comprises a highly stereoselective acetylation step of 1-methylacetonide, and the pure β-anomer thus obtained can be advantageous used for preparing capecitabine.
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Page/Page column 8-11
(2008/12/07)
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- The synthesis of (-)-varitriol and (-)-3′-epi-varitriol via a Ramberg-B?cklund route
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A concise route to the anti-tumour natural product (-)-varitriol, together with its novel isomer (-)-3′-epi-varitriol, is described using a Horner-Wadsworth-Emmons (HWE)/conjugate addition/Ramberg-B?cklund sequence as the cornerstone. The flexibility of t
- McAllister, Graeme D.,Robinson, James E.,Taylor, Richard J.K.
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p. 12123 - 12130
(2008/02/11)
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- Adenosine kinase inhibitors. 6. Synthesis, water solubility, and antinociceptive activity of 5-phenyl-7-(5-deoxy-β-d-ribofuranosyl) pyrrolo[2,3-d]pyrimidines substituted at C4 with glycinamides and related compounds
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4-(Phenylamino)-5-phenyl-7-(5-deoxy-β-D-ribofuranosyl)pyrrolo[2,3-d] pyrimidine (1) and related compounds known as "diaryltubercidin" analogues are potent inhibitors of adenosine kinase (AK) and are orally active in animal models of pain such as the rat formalin paw model (GP3269 ED 50 = 6.4 mg/kg). However, the utility of this compound class is limited by poor water solubility that can be attributed to the high energy of crystallization caused by stacking of the parallel C4 and C5 aryl rings in the solid state (compound 1 and GP3269 each with pH 7.4 solubility 50 = 3 nM and water solubility = 32 ± 9 μg/mL at pH 7.4), was further characterized in biological assays. Compound 16c exhibited strong oral efficacy in the rat formalin paw model (ED50 of 2.5 mg/kg). In the most advanced assay, 16c was found to inhibit bradykinin-induced licking in marmoset monkeys with an ED50 estimated at 0.9 mg/kg without producing evidence of side effects such as ataxia, sedation, and emesis at this dose. However, lethal toxicity in the rat formalin paw model occurred with high doses of 16c, and further work on this series was discontinued.
- Bookser, Brett C.,Ugarkar, Bheemarao G.,Matelich, Michael C.,Lemus, Robert H.,Allan, Matthew,Tsuchiya, Megumi,Nakane, Masami,Nagahisa, Atsushi,Wiesner, James B.,Erion, Mark D.
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p. 7808 - 7820
(2007/10/03)
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- The first synthesis and determination of absolute stereochemistry of clonostachydiol - Part II
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The first total synthesis of clonostachydiol has been achieved from two appropriately protected hydroxy acids that are derived from (D)-xylose and 1,2-O-isopropylidene (D)-glyceraldehyde.This synthesis has proved the absolute configuration of four stereoc
- Rao, A. V. Rama,Murthy, V. S.,Sharma, G. V. M.
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p. 143 - 146
(2007/10/02)
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- An Efficient Synthesis of 5-Deoxy-D-ribohexose
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5-Deoxy-D-ribohexose (1) has been obtained from methyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside via Wittig reaction with methoxymethylenetriphenyl phosphorane and subsequent hydrolytic and deprotection steps. 13C NMR spectrum show, that 1 occurs as two furanoses, two septanoses and an aldehydo form.Peracetylation of 5-deoxy-D-ribohexose leads to both furanose forms and, most probably, to an α-septanose ring.Key words: 5-deoxy-D-ribohexose, Wittig reaction
- Pakulski, Z.,Zamojski, A.
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p. 912 - 917
(2007/10/02)
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