4064-06-6Relevant articles and documents
Reductive Cleavage of Sulfonates. Deprotection of Carbohydrate Tosylates by Photoinduced Electron Transfer
Masnovi, John,Koholic, Dolores J.,Berki, Robert J.,Binkley, Roger W.
, p. 2851 - 2853 (1987)
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Rapid synthesis of 1-deoxygalactonojirimycin using a carbamate annulation
Timmer, Mattie S.M.,Dangerfield, Emma M.,Cheng, Janice M.H.,Gulab, Shivali A.,Stocker, Bridget L.
, p. 4803 - 4805 (2011)
A remarkably efficient synthesis of the biologically important iminosugar 1-deoxygalactonojirimycin (DGJ) is presented. Key to this strategy is the development of a novel carbamate annulation reaction that favours formation of a six-membered carbamate-containing piperidine skeleton over its five-membered counterpart.
Ready preparation of sugar acetals under ultrasonic irradiation
Einhorn, Cathy,Luche, Jean-Louis
, p. 258 - 261 (1986)
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Thermoresponsive copolymers with pendant d-galactosyl 1,2,3-triazole groups: Synthesis, characterization and thermal behavior
Dhumure, Archana B.,Patil, Ajay B.,Kulkarni, Anuja S.,Voevodina, Irina,Scandola, Mariastella,Shinde, Vaishali S.
, p. 8179 - 8187 (2015)
A galactose containing glycomonomer has been synthesized by copper catalyzed azide-alkyne cyclo-addition reaction (CuAAC) of 6-azido-6-deoxy-1,2:3,4-di-O-isopropylidene-α-d-galactopyranose with propargyl acrylate. This monomer was subjected to homopolymerization and copolymerization with N-isopropylacrylamide (NIPAm) at different compositions by free radical polymerization using 2,2′-azobis-isobutyronitrile (AIBN) as an initiator. The composition of the copolymer was determined by 1H-NMR spectroscopy. Upon acid hydrolysis of acetonide protected polymers, water-soluble deprotected polymers were obtained. The polymers were characterized and confirmed by NMR, IR, GPC and thermal analytical techniques. The protected and deprotected copolymers showed a sharp cloud-point temperature and a linear correlation was obtained between the lower critical solution temperatures (LCST) and the concentration of glycomonomer in the copolymers. This allows tuning the thermal response by simply altering the copolymer composition. Water contact angle experiments showed the changes in the hydrophilicity of copolymers with compositions that supported the LCST results. The glass transition temperature of protected copolymers followed a regular monotonic decreasing trend with increasing glycomonomer content, whereas Tg of deprotected copolymers increased due to H-bond interaction. The attempts to develop thermoresponsive polymers having LCSTs at physiological temperature were successful.
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Horton et al.
, p. 56,62 (1968)
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Synthesis, spectroscopic studies, and x-ray crystallographic analysis of the organotin carbohydrate: 1,2:3,4-di-O-isopropylidene-6-O-triphenylstannylmethyl-α-D-galactopyranose
Cox, Philip J.,Melvin, Olga A.,Garden, Simon J.,Wardell, James L.
, p. 469 - 476 (1995)
The title organotin carbohydrate, C31H36O6Sn, has been synthesized and its molecular structure has been determined in solution and in the solid state.NMR, infrared, mass and X-ray crystallographic techniques were used.The chiral molecules crystallize in the monoclinic space group P21 with Z=2.The triphenyltin and carbohydrate moieties are linked by a trans methylene-oxygen-methylene arrangement.The pyranosyl ring adopts a twist-boat conformation and the isopropylidene rings adopt different (half-chair and envelope) forms.Solution and solid-state conformations are similar as only three Δ 13C shift values are greater than 2ppm; the Δ 119Sn value is 12 ppm.KEY WORDS: X-ray crystallographic analysis; organotin; carbohydrate.
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Dmitriev et al.
, p. 25,26-34 (1976)
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Epoc group: Transformable protecting group with gold(iii)-catalyzed fluorene formation
Chang, Tsung-Che,Tanaka, Katsunori,Yamamoto, Tomoya
, p. 10703 - 10709 (2021/08/24)
This study presents the novel concept of a transformable protecting group, which changes its properties through structural transformation. Based on this concept, we developed a 2-(2-ethynylphenyl)-2-(5-methylfuran-2-yl)-ethoxycarbonyl (Epoc) group. The Epoc group was transformed into an Fmoc-like structure with gold(iii)-catalyzed fluorene formation and was removable under Fmoc-like mild basic conditions post-transformation even though it was originally stable under strongly basic conditions. As an application for organic synthesis, the Epoc group provides the novel orthogonality of gold(iii)-labile protecting groups in solid-phase peptide synthesis. In addition, the high turnover number of fluorene formation in aqueous media is suggestive of the applicability of the Epoc group to biological systems. This journal is
Synthesis and applications of carbohydrate based chiral ionic liquids as chiral recognition agents and organocatalysts
Kaur, Nirmaljeet,Chopra, Harish Kumar
, (2019/11/26)
Chiral ionic liquids (CILs) have shown a wide range of applications in variety of domains in chemistry. Because of this, synthesis and applications of CILs have always been areas of interest for research in the last 20 years. Present work describes, the synthesis of six carbohydrate based chiral ionic liquids (CCILs) by following simple procedures and their applications. Structures of the CCILs were confirmed through various analytical techniques like NMR spectroscopy (1H, 13C, 11B, 31P, 19F), EI-MS, and polarimetry. Designed CCILs were tested as chiral recognising agents using sodium salt of Mosher's acid as model substrate through 19F NMR spectroscopy. Further, CCILs were used as organocatalyst in the enantioselective reduction of aromatic prochiral ketones to achieve corresponding chiral secondary alcohols.
D-galactose-based organogelator for phase-selective solvent removal and sequestration of cationic dyes
Goel, Shubhra,Jacob, Josemon
, (2020/11/03)
Naturally occurring sugar-based monomers are attractive substrates in the design of functional glycopolymers. In this study, we report on the development of D-galactose based organogels of varying crosslink density capable of selective adsorption of dyes and solvents. Free radical polymerization of 6-O-methacryloyl-1,2;3,4-di-O-isopropylidene-D-galactose in the presence of nonamethylene glycoldimethacrylate generated novel crosslinked polymers OG10, OG15 and OG20 with 10, 15 and 20 wt% crosslinker, respectively. Depending on the nature of the solvent, OG10 undergoes swelling upto 935%. The negative zeta potential, as determined from DLS measurements, and the gelation ability suggested the potential utility of the polymer for dye removal from water. OG10 displayed significant adsorption of rhodamine B (RhB) (>95%), crystal violet (>93%), and methylene blue (>70%) dyes as well as the selective adsorption of >90% RhB from a solution containing both RhB and methyl orange. These porous organogels are also found to be suitable for phase-selective removal of organic solvents.