Glycoside aminomethyl

Similarly, per-O-trimethylsilylated mono- and P-linked disaccharides (lactose and cellobiose, not melibiose) could be converted into the corresponding a-glycosyl iodides, which upon SN2 displacement with CbT using TBACN mainly afforded P-cyano derivatives in good overall yields [191]. The cyanoglycosides were transformed into aminomethyl glycosides via reduction under mild conditions (Scheme 2.52). 

Drew, K N, Gross, P H, C-glycoside syntheses. II. Henry condensations of 4,6-0-alkylidene pyranoses with a 1,3-proton transfer catalyst — a route to blocked aminomethyl-C-glycosides, Tetrahedron, Al, 6113-6126, 1991. 

Otherwise aminomethyl -glycoside derivatives may be obtained by reduction of glycosyl cyanides (Chapters 21, 22)." Condensation of enamines of j9-ketoesters and ketones with tetra-Q-benzyl-a-D-glucopyranosyl chloride activated with silver triflate gave a-C-glucosides as epimeric mixtures in 80-85% yield (Scheme 15). ... 

An aminomethyl C-glycoside derivative is mentioned in Chapter 3. The burgeoning interest in cyclic imino-alditol derivatives is reflected in many papers in this field. ef-Homonojirimycin (2,6-di-deoxy-2.6-imino-D-glycero-L-gulo-heptitol)(8) has been isolated from... 

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