The Journal of organic chemistry

Multiple and Regioselective Introduction of Protected Sulfates into Carbohydrates Using Sulfuryl Imidazolium Salts

AY Desoky, SD Taylor

Index: Ingram, Laura J.; Desoky, Ahmed; Ali, Ahmed M.; Taylor, Scott D. Journal of Organic Chemistry, 2009 , vol. 74, # 17 p. 6479 - 6485

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Citation Number: 11

Abstract

Selective incorporation of trichloroethyl (TCE)-protected sulfates into monosaccharides was examined using reagent 2. In general, sulfation of 4, 6-O-benzylidene acetals of galactosides and glucosides (2-OH versus 3-OH sulfations) proceeded in good to excellent yield and selectivity. Sulfation occurred predominantly at the 2-OH in 4, 6-O-benzylidene acetals of α-glucosides and at the 3-OH in 4, 6-O-benzylidene acetals of β-galactosides ...