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ChemInform Abstract: Stereoselective Synthesis of 2′,3′-Dideoxy-nucleosides via Intramolecular Glycosylation of Phenyl 1-Seleno-glycosides. Synthesis of 2′,3′-Dideoxythymidine.

✍ Scribed by J. LLUIS; M. I. MATHEU; S. CASTILLON

Publisher
John Wiley and Sons
Year
2010
Weight
34 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

Stereoselective Synthesis of 2',3'-Dideoxy-nucleosides via Intramolecular Glycosylation of Phenyl 1-Seleno-glycosides.

Synthesis of 2',3'-Dideoxythymidine.

-The intramolecular glycosylation of the coupling products (III) is examined. However, treatment with AgO-Tf and NaOH results only in the isolation of the hydrolysis products (IV). The presence of the silyl protecting group in the base is found to be necessary leading to the β-anhydro nucleoside (V) from (IIIa). Final hydrolytic ring opening affords 3'-deoxythymidine with complete stereocontrol. -(LLUIS,

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