ChemInform Abstract: Synthetic Approaches to 3′-Azido-3′-deoxythymidine and Other Modified Nucleosides.
Abstract
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ChemInform Abstract
Reaction of the siloxybutadiene (I) with trimethyl orthoformate (II) forms the aldehyde acetal (III) which is converted diastereoselectively to the epoxide (IV). Treatment with trimethylsilyl azide (V) produces the azido diol (VI) which is cyclized and silylated to yield the azido sugar (VIII). Coupling with bis(trimethylsilyl)thymine (IX) and desilylation produces β-AZT ( X), together with the α-anomer (XI).
