Abstract
2-(Trimethylsilyl) ethyl (TMSET) glycosides were transformed in high yields into the corresponding1-chloro sugars by treatment with 1,1-dichloromethyl methyl ether/zinc chloride. With acetyl, benzoyl, and benzyl protection of the 2-position, the α-glycopyranosyl chloride was the major product, whereas with the 2-phthalimido sugar, a β-chloride was obtained. The fully benzylated TMSET glucopyranoside gave a α-chloro sugar carrying a 6-O-formyl group whereas partially benzylated sugars gave the chloro sugars with all protecting groups intact
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