An asymmetric approach to 2-deoxynucleosides via organosulfur building blocks as chemical chameleons.

B M Trost, C Nübling

Index: Carbohydr. Res. 202 , 1-12, (1990)

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Abstract

An asymmetric synthesis of 6-N-benzoyl-5'-O-benzyl-2'-deoxyadenosine and its a anomer from non-carbohydrate building blocks is achieved in 7 steps. The sequence builds the basic structures using bis(methylthio)methane and methylthiomethyl phenyl sulfone as both nucleophilic and electrophilic building blocks, a feature that suggests their behavior as chemical chameleons. The asymmetric induction is achieved utilizing a kinetic resolution based upon catalytic asymmetric epoxidation.