Concise and stereospecific synthesis of novel bicyclic dideoxynucleosides as potential antiviral agents

A novel class of dideoxynucleosides containing a bicyclic sugar moiety, structurally related to the natural griseolic acids, was synthesized starting from the stereochemically defined compound, 1,4:3,6-dianhydro-D-glucitol. The key intermediate in the synthesis was a [3.3.0] fused bicyclic glycal. G...

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Bibliographic Details
Published inTetrahedron Vol. 54; no. 13; pp. 3113 - 3124
Main Authors Chao, Qi, Zhang, Jianzhong, Pickering, Lea, Jahnke, Tamera S., Nair, Vasu
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 26.03.1998
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
NUCLEOSIDE ANALOGS
STABILITY
CARBOCYCLIC THYMIDINE
INHIBITORS
DUPLEX
DERIVATIVES
GRISEOLIC ACID
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Summary:A novel class of dideoxynucleosides containing a bicyclic sugar moiety, structurally related to the natural griseolic acids, was synthesized starting from the stereochemically defined compound, 1,4:3,6-dianhydro-D-glucitol. The key intermediate in the synthesis was a [3.3.0] fused bicyclic glycal. Glycosylation of this compound with nucleobase proceeded both regiospecifically and stereospecifically in the presence of an auxiliary agent, N-iodosuccinamide. Changes in stereochemistry during the synthesis was monitored by optical rotation data and confirmed by both 1D and 2D NMR experiments. The synthetic approach described possesses general usefulness. Development of approaches to the synthesis of new nucleosides with bicyclic carbohydrate moieties (B = nucleobases)
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(98)00061-1