Bioorganic & Medicinal Chemistry Letters 2009-06-01

(S)-Camphorsulfonic acid catalyzed highly stereoselective synthesis of pseudoglycosides.

Bala Kishan Gorityala, Shuting Cai, Jimei Ma, Xue-Wei Liu

Index: Bioorg. Med. Chem. Lett. 19(11) , 3093-5, (2009)

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Abstract

A mild and efficient synthesis of pseudoglycosides has been developed using metal free (S)-camphorsulfonic acid. (S)-CSA acts as an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-D-glucal to 2,3-unsaturated O-glycosides. A wide range of biologically active natural products, alcohols and thiols could be coupled with glucal to give the desired pseudoglycosides in good to excellent yields with exclusive alpha-stereoselectivity.