Per-O-acetylated glycopyranosyl

Figure 1. The distribution of the 35Cl NQR frequencies of per-O-acetylated glycopyranosyl chlorides...

Condensation of the appropriate per-O-acetylated glycopyranosyl bromide with 4-aminobenzenethiol in the presence of sodium methoxide has been used to prepare 4-aminophenyl l-thio-j3-D-gluco-, -galacto-, and -xylo-pyranosides and 4-aminophenyl 2-acetamido-2-deoxy-1 -thio-jS-D-glucopyranoside. 4-Amino-phenyl l-thio-/3-D-glucopyranosiduronic acid was synthesized by condensation of methyl (2,3,4-tri-O-acetyI-a-D-glucopyranosyl bromide)uronate with 4-aminobenzenethiol, followed by saponification with sodium hydroxide. An attempt to obtain the l,2-ci5-l-thioaldopyranoside by reaction of 4,6-di-0-acetyl-2,3-0-carbonyl-a-D-mannopyranosyl bromide (191) with sodium 4-nitrobenzene-... 

Several 9-glycopyranosylpurin-6(l/T)-one derivatives, with xylopyranosyl, glucopyranosyl, 2,3,4,6-tetra-O-acetylglycopyranosyI, or 2,3,4-tri-O-xylopyranosyl as the glycosyl moiety, are obtained by reaction of formimidamide acetate with 5-amino-6-(glycopyranosylamino)pyrimidin-4(3//)-ones or 5-amino-6- [(per-0-acetyl)glycopyranosyl]amino pyrimidin-4(3T/)-ones, respectively. The reaction conditions are mild and good yields are obtained, e.g. formation of 12. ... 

A synthetic way to incorporate monosaccharides (o-glucose, D-galactose) and oligosaccharides (lactose, maltose, maltotriose) into [60]fullerene by thermolysis of per-O-acetyl glycosyl azides in the presence of fullerene (Scheme 23) was reported by Kobayashi [93]. This procedure, based on the cycloaddition reaction of alkyl azides with fullerenes [94], gave a mixture of two inseparable stereoisomers of N-b-glycopyranosyl azafulleroids in moderate 13-28% yields. 

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