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Synthesis of (5R)- and (5S)-5-Methyl-5, 6-dihydrouridine Derivatives by Vinko Škarić; Jasenka Matulić-Adamić is a Chemistry article available to read on EtoBox.
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## 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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- Author
- Vinko Škarić; Jasenka Matulić-Adamić
- Publisher
- John Wiley and Sons; Wiley (John Wiley & Sons); Wiley-Blackwell; Wiley (ISSN 0018-019X)
- Published
- 1983
- Language
- EN
- Field
- Chemistry (Physical Sciences)