Synthesis of novel 3′-C-methyl-apionucleosides: an asymmetric construction of a quaternary carbon by Claisen rearrangement

JH Hong, MY Gao, Y Choi, YC Cheng, RF Schinazi…

Index: Hong, Joon H.; Gao, Mu-Yun; Choi, Yongseok; Cheng, Yung-Chi; Schinazi, Raymond F.; Chu, Chung K. Carbohydrate Research, 2000 ,  vol. 328,  # 1  p. 37 - 48

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Citation Number: 25

Abstract

The synthesis of 2, 3-dideoxy-3-C-(hydroxymethyl)-3-C-methyl-d-glycero-tetrofuranosyl nucleosides was accomplished in high enatiomeric purity (98.5% ee) via [3, 3]-sigmatropic Claisen rearrangement of (E)(S)-5-benzyloxy-1-tert-butyldimethylsilanyloxy-4-methyl-pent-3- en-2-ol prepared from 2, 3-O-isopropylidene-d-glyceraldehyde. The synthesized nucleosides were assayed against human immunodeficiency virus (HIV) and hepatitis B ...