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- Title
Synthesis of 5-Methyluridine and Its 5′-Mercapto-, 2-Amino-, and 4′,5′-Unsaturated Analogues.
- Authors
Škarié, Vinko; Matulié-Adamié, Jasenka
- Abstract
The stereospecific cis-hydroxylation of 1-(2,3-dideoxy-β- D-glyceropent-2-enofuranosyl)thymine (1) into 1-β- D-ribofuranosylthymine (2) by osmium tetroxide is described. Treatment of 2′,3′- O, O-isopropylidene-5-methyl-2,5′-anhydrouridine (8) with hydrogen sulfide or methanolic ammonia afforded 5′-deoxy-2′,3′- O, O-isopropylidene-5′-mercapto-5-methyluridine (9) and 2′,3′- O, O-isopropylidene-5-methyl-isocytidine (10), respectively. The action of ethanolic potassium hydroxide on 5′-deoxy-5′-iodo-2′,3′- O, O-isopropylidene-5-methyluridine (7) gave rise to the corresponding 1-(5-deoxy-β- D-erythropent-4-enofuranosyl)5-methyluracil (13) and 2- O-ethyl-5-methyluridine (14). The hydrogenation of 2 and its 2′,3′- O, O-isopropylidene derivative 4 over 5% Rh/Al2O3 as catalyst generated diastereoisomers of the corresponding 5-methyl-5,6-dihydrouridine ( 17 and 18).
- Publication
Helvetica Chimica Acta, 1980, Vol 63, Issue 8, p2179
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19800630808