Glycopyranosides synthesis

A. K. Misra, P. Tiwari, and G. Agnihotri, Ferrier rearrangement catalyzed by HC104-Si02 Synthesis of 2,3-unsaturated glycopyranosides, Synthesis, 2 (2005) 260-266. 

U. Aich and D. Loganathan, Stereoselective single-step synthesis and X-ray crystallographic investigation of acetylated aryl 1, 2-trans glycopyranosides and aryl 1,2-cis C2-hydroxy-glycopyranosides, Carbohydr. Res., 341 (2006) 19-28. 

T. Granier and A. Vasella, Synthesis and evaluation as glycosidase inhibitors of I //-iinidazol-2-yl C-glycopyranosides, Helv. Chim. Acta, 78 (1995) 1738—1746. 

The first synthesis of methyl 4-thiomaltoside (36b) (34%), 4-thiocellobioside (39d) (52%) and 4-thiodigalactobioside (86) (56%) was reported 18 years ago by using the Sn2 displacement of 1,2-cis- or 1,2-trans- glycosyl halides (9 a), (7 a) and (7c) with methyl 4-thio-a-D-glycopyranoside sodium salts generated from the acetylated methyl glycosides (84) and (85a) (Scheme 25) [14a]. 

B. Fraser-Reid and B. J. Carthy, Synthesis of some a-cyclopropylcarbonyl glycopyranosides, Can. J. Chem. 50 2928 (1972). 

Sakurai et al. as well as Sandhoff et al. used this approach for the synthesis of allyl-C-glycopyranosides 21 from readily accessible peracetylated or perbenzylated glycopyranoses 19 [12, 13]. Addition of allylsilane to oxonium 20 proceeds with an axial/equatorial selectivity that is considerably affected by the polarity of the solvent (Scheme 13.9). 

Synthesis of Alkyl 2-Deoxy-a-D-glycopyranosides and Their 2-Deuterio Derivatives, R. U. Lemieux and S. Levine, Can. J. Chem., 42 (1964) 1473-1480. 

C. Leteux and A. Veyrieres, Synthesis of a-C-glycopyranosides of D-galactosamine and D-glucosamine via iodocyclization of corresponding glycals and silver tetrafluoroboranuide-promoted alkynylation at the anomeric center, J. Chem. Soc., Perkin Trans. 1, (1994) 2647-2655. 

Schmidt and Wernicke74 have described a synthesis of digitalose starting with D-fucose dibenzyl mercaptal, which on condensation with acetone yielded the 4,5-isopropylidene derivative (LXXIV). Elimination of the dibenzyl mercaptal residues with mercuric chloride and cadmium carbonate in methanol gave 4,5-isopropylidene-D-fucose dimethylacetal (LXXV), from which the 2-benzyl ether was obtained on treatment with sodium and benzyl chloride. Methylation produced 2-benzyl-3-methyl-4,5-iso-propylidene-D-fucose dimethyl acetal (LXXVI), from which the iso-propylidene group was eliminated on treatment with methanolic hydrogen chloride, which also effected glycopyranoside formation (LXXVII). The... 

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