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  • Title: Efficient synthesis of omega-mercaptoalkyl 1,2-trans-glycosides from sugar peracetates.
    Author: Murakami T, Hirono R, Sato Y, Furusawa K.
    Journal: Carbohydr Res; 2007 Jun 11; 342(8):1009-20. PubMed ID: 17362892.
    Abstract:
    Lewis acid-promoted reactions of peracetylated sugars (glucose, galactose, maltose, lactose) with omega-bromo-1-alkanols (C(8), C(12)) were investigated. ZnCl(2) was found to promote the 1,2-trans-glycosylation of the alcohols in toluene at about 60 degrees C in a stereocontrolled manner with better yields than commonly employed promoters such as SnCl(4). The omega-bromoalkyl acetylated glycosides were readily converted to omega-mercaptoalkyl glycosides, which are useful for the preparation of glycoclusters.
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