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Synthesis of (5R)- and (5S)-5-Methyl-5, 6-dihydrouridine Derivatives

✍ Scribed by Vinko Škarić; Jasenka Matulić-Adamić

Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
453 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The hydrogenation of 2′, 3′‐O‐isopropylidene‐5‐methyluridine (1) in water over 5% Rh/Al~2~O~3~ gave (5 R)‐ and (5 S)‐5‐methyl‐5, 6‐dihydrouridine (2), separated as 5′‐O‐(p‐tolylsulfonyl)‐ (3) and 5′‐O‐benzoyl‐ (5) derivatives by preparative TLC. on silica gel and ether/hexane developments. The diastereoisomeric differentiation at the C(5) chiral centre depends upon the reaction media and the nature of the protecting group attached to the ribosyl moiety.

The synthesis of iodo derivatives (5 R)‐ and (5 S)‐4 is also described. The diastereoisomers 4 were converted into (5 R)‐ and (5 S)‐2′, 3′,‐O‐isopropylidene‐5‐methyl‐2, 5′‐anhydro‐5, 6‐dihydrouridine (7).

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