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Synthesis of 1 -[2,3-dideoxy-3-(3-hydroxypropyl)-D-pentofuranosyl]thymines

✍ Scribed by Walczak, Krzysztof ;Pupek, Krzysztof ;Pedersen, Erik B.

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
419 KB
Volume
1991
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Free radicals generated by reaction of protected methyl 2,3‐ dideoxy‐3‐iodopentofuranosides 2, 3, and 9 with tributyltin hydride in the presence of a radical initiator (AIBN) were treated with acrolein to give methyl 2,3‐dideoxy‐3‐(3‐oxopropyl)pentofuranosides 4 and 5. Reduction of 5 with Sodium borohydride followed by protection of hydroxy groups by reaction with tert‐butyl chlorodiphenylsilane gave the carbohydrate derivative 11 which was condensed with silylated thymine to afford a separable mixture of α‐ and β‐nucleosides 13 and 14. These nucleosides were subsequently deprotected to give the 3′‐propyl‐extended thymidine 16 and its corresponding α‐isomer 15.

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