Original scientific paper

Stereoselective Transformations in the Thymidine Series

V. Škarić ; Laboratory of Stereochemistry and Natural Products, "Rudjer Boskovic« Institute, 41001 Zagreb, Croatia, Yugoslavia
M. Pavela-Vrančič ; Laboratory of Stereochemistry and Natural Products, "Rudjer Boskovic« Institute, 41001 Zagreb, Croatia, Yugoslavia
J. Matulić-Adamić ; Laboratory of Stereochemistry and Natural Products, "Rudjer Boskovic« Institute, 41001 Zagreb, Croatia, Yugoslavia

Abstract

The s tereoselective 5% Rh/ AliOa hydrogenations Olf .thymidine,
3',5'-anhydro- X and 3'-deoxy- XII thymidines to -the
corresipondiing (5S) - 5,6-d1hydirothymi!di..ne deirivaitiv1es I, IX, and
XIII were evLdenced by 1H- and 13C-NMR analyses and N-.glycosidix!
bo1I1d cleaV'ages .to (-)-S-5,6-dihydrot:hymine. Th:e regiose
·lect.ive syntiheses 01f the configuraotionally defined (58)-5'-
0-tosyl- (Ill) and (5'S)-5'-deoxy-5'-iodo- (IV) 5,6-dihydrothymidines
aire descriibed. The tntramolecular cyC'lisat.ion of (5S) - 3',5'-dimesyloxy-5,6- -dihydrothymidine (II) by NaiOMe afforded (5R,5S)-5'-0-mesy.I- -2,3' -anhydro- 5,6-dihydrothym.idines 5,6-Dihydropyrimidine

Keywords

Hrčak ID:

194146

URI

https://hrcak.srce.hr/194146

Publication date:

15.9.1984.

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