Facile preparation of protected furanoid glycals from thymidine

MA Cameron, SB Cush…

Index: Cameron, Melissa A.; Cush, Sarah B.; Hammer, Robert P. Journal of Organic Chemistry, 1997 , vol. 62, # 26 p. 9065 - 9069

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Citation Number: 52

Abstract

The synthesis of O-silyl-and O-acyl-protected furanose glycals from free thymidine was investigated. The method of glycal formation reported by Pedersen et al. was successfully expanded to include 5-ester (toluoyl) protected glycals as well as various combinations of 5'- ester and 3-and 5-tert-butyldimethylsilyl and tert-butyldiphenylsilyl protection. Gram quantities of furanoid glycals can be prepared in a few days in two-four synthetic steps in ...