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Stereoselective synthesis of 2′,3′-dideoxy-nucleosides via intramolecular glycosylation of phenyl 1-seleno-glycosides. Synthesis of 2′,3′-dideoxythymidine

✍ Scribed by Jordi Lluís; MaIsabel Matheu; Sergio Castillón

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 230 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)00093-8

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✦ Synopsis

4-methoxy and 4-(2-trimethylsilylethoxy)pyrimidine bases were attached to the 5position of the phenyl 2,3-dideoxy-l-seleno-glycero-pentofuranoside moiety. The presence of the silyl protecting group in the base is necessary to lead to neutral 13-anhydro nucleosides by inlramolecular glycosylafion. The subsequent ring opening affords 3'-deoxythymidine with complete stereocontrol.

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