University of California

Matthew Schombs

Jacquelyn Gervay-Hague

Wenjun Du

Suvarn Subhash Kulkarni

The present invention provides novel, regioselectively-acylated oligosaccharide compounds and methods for preparing them. In another aspect, the invention provides a method for preparing a selectively-acylated oligosaccharide. The method includes forming a reaction mixture containing a protected oligosaccharide and an acylating agent. The protected oligosaccharide includes at least three hydroxyl moieties and each hydroxyl moiety is protected with a silyl protecting group. The reaction mixture is formed under conditions sufficient to selectively replace at least one silyl protecting group with a &#x2014;C(0)-C1_6 alkyl group, and the selectively-acylated oligosaccharide comprises at least one &#x2014;C(0)-C1_6 alkyl group and at least one silyl protecting group.

Regioselective silyl exchange of per-silylated oligosaccharides

The present invention provides novel, regioselectively-acylated oligosaccharide compounds and methods for preparing them. In another aspect, the. invention provides a method for preparing a selectively-acylated oligosaccharide. The method includes forming a reaction mixture containing a protected oligosaccharide and an acylating agent. The protected oligosaccharide includes at least three hydroxyl moieties and each hydroxyl moiety is protected with a silyl protecting group. The reaction mixture is formed under conditions sufficient to selectively replace at least one silyl protecting group with a &#x2014;C(0)-C1_6 alkyl group, and the selectively-acylated oligosaccharide comprises at least one &#x2014;C(0)-C1_6 alkyl group and at least one silyl protecting group.

The present invention provides a one-pot method of preparing an unprotected &#x3b1;-O-glycolipid. The first step involves contacting a protected &#x3b1;-iodo sugar with a catalyst and a lipid comprising a hydroxy group, under conditions sufficient to prepare a protected &#x3b1;-O-glycolipid. The second step involves deprotecting the protected &#x3b1;-O-glycolipid under conditions sufficient to prepare the unprotected &#x3b1;-O-glycolipid, wherein the contacting and deprotecting steps are performed in a single vessel. The present invention also provides a one-pot method of preparing an unprotected &#x3b2;-O-glycolipid following the steps for the preparation of the unprotected &#x3b1;-O-glycolipid.

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Oxford, United Kingdom

Matthew Schombs