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. 2010 Apr 12;49(17):3049-52.
doi: 10.1002/anie.200907178.

Stereoselective synthesis of alpha-keto-deoxy-D-glycero-D-galacto-nonulosonic acid glycosides by means of the 4,5-O-carbonate protecting group

David Crich  1 , Chandrasekhar Navuluri
Affiliations

Stereoselective synthesis of alpha-keto-deoxy-D-glycero-D-galacto-nonulosonic acid glycosides by means of the 4,5-O-carbonate protecting group

David Crich et al. Angew Chem Int Ed Engl. .

Abstract

A 1-adamantyl thioglycoside derivative of KDN, derived from N-acetylneuraminic acid, carrying a 3,4-O-carbonate protecting group is a highy efficient and α-selective KDN donor on activation with NIS and TfOH in dichloromethane and acetonitrile at −78 °C. Glycosylations conducted with this protecting group do not suffer from competing glycal formation. Seven examples are given, including the use of galactose 3- and 6-hydroxy groups.

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Figures

Figure 1
Figure 1
Hypothetical Intermediate Stabilized by the Presence of the Cyclic Carbonate
Scheme 1
Scheme 1
Donor synthesis. Ada = 1-adamantanyl, pTSA = para-toluenesulfonic acid.
Scheme 2
Scheme 2
Synthesis of an authentic sample of glycal. mCPBA = meta-chloroperoxybenzoic acid.
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