A highly stereoselective synthesis of anti-HIV 2', 3'-dideoxy-and 2', 3'-didehydro-2', 3'-dideoxynucleosides

JW Beach, HO Kim, LS Jeong, S Nampalli…

Index: Beach, J. Warren; Kim, Hea O.; Jeong, Lak S.; Nampalli, Satyanarayana; Islam, Qamrul; et al. Journal of Organic Chemistry, 1992 ,  vol. 57,  # 14  p. 3887 - 3894

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Citation Number: 87

Abstract

A general total synthetic method for the stereocontrolled synthesis of 2', 3 '-dideoxy-as well as 2 ', 3'-di-dehydro-2', 3'-dideoxynucleosidea is presented. Introduction of an a- phenylselenenyl group at the 2-position of 2, 3-dideoryriboeyl acetate directs the glycosyl bond formation to give 295% &isomer. This 2'-phenylselenenyl nucleoside may be converted to either the 2', 3'-dideoxynucleoside by treatment with n-Bu3SnH and E@ at ...