Synthesis of 2′,3′-Dideoxypurinenucleosides via the Palladium Catalyzed Reduction of 9-(2,5-Di-O-acetyl-3-bromo-3-deoxy-β-d-xylofuranosyl)purine Derivatives

Autor:	Hiroshi Shiragami, Masayuki Arai, Toshihide Yukawa, Y. Amino, Kunisuke Izawa, Yutaka Honda, Yasuhiro Tanaka, Hisao Iwagami
Rok vydání:	1996
Předmět:	chemistry.chemical_classification Reaction mechanism Base (chemistry) Stereochemistry Leaving group chemistry.chemical_element Biochemistry Catalysis Thymine Solvent chemistry.chemical_compound chemistry Genetics Purine metabolism Palladium
Zdroj:	Nucleosides and Nucleotides. 15:31-45
ISSN:	0732-8311
DOI:	10.1080/07328319608002368
Popis:	Practical method to produce 2′,3′-dideoxypurinenucleosides from 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)purines (1) was developed. High ratio of 2′,3′-dideoxynucleoside to 3′-deoxyribonucleoside was obtained by selecting the reaction conditions (solvent, pH and/or base), or changing 2′-acyloxy leaving group. The reaction mechanism was studied by deuteration experiments of 1a and 1-(3,5-di-O-acety1-2-bromo-2-deoxy-β-D-ribofuranosyl)thymine (12). †Dedicated to Dr. Yoshihisa Mizuno on the occasion of his 75th birthday.
Databáze:	OpenAIRE
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