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Synthesis of 5-deuteromethyl-2′-deoxyuridine (thymidine-α,α,α-d3) and related compounds

✍ Scribed by C.-Y. Shiue; A. P. Wolf; D. N. Slatkin

Publisher: John Wiley and Sons
Year: 1980
Tongue: French
Weight: 289 KB
Volume: 17
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580170204

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✦ Synopsis

Abstract

Thymine‐α,α,α‐d~3~ (4) was synthesized from perdeuterated methyl iodide and pyrimidine‐lithium. Thymidine‐α,α,α‐d~3~ (8) was then synthesized by coupling compound 4 with 1α‐chloro‐2‐deoxy‐3,5‐bis(p‐toluoyl)‐α‐D‐ribofuranosyl chloride in the presence of Friedal‐Crafts catalyst. Thymidine‐α,α,α‐d~3~ (8), a metabolic precursor of deoxyribonucleic acid, has potential application for study of human tissue growth kinetics in vivo using a sensitive deuterium micromapping technique.

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