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Synthesis of 2′,5′-Dideoxyuridine-5′-phosphonates

✍ Scribed by Aly, Youssef L. ;Abdel-Megied, Ahmed E.-s. ;Pedersen, Erik B. ;Nielsen, Claus

Book ID
102368506
Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
266 KB
Volume
1992
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Methyl 2,5‐dideoxy‐5‐iodo‐3‐O‐pivaloyl‐D‐erythro‐pentofur‐anoside (5) was synthesized from 2‐deoxy‐D‐ribose and treated with triethyl phosphite to give the phosphonate 6. Reaction of 6 with silylated 2,4‐dihydroxypyrimidine 7 in the presence of trimethylsilyl trifluoromethanesulfonate as catalyst afforded nucleoside phosphonates 8 and 9 which were deprotected with C~2~H~5~ONa in ethanol to give the diethyl 2′,5′‐dideoxyuridine‐5′‐phosphonate 10 and its α‐anomer 11. No activity was found for the nucleosides 8–11 against HIV or HSV‐1.

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