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

Article abstract of DOI:10.1080/07328319608002368

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-acetyl-2-bromo-2-deoxy-β-D-ribofuranosyl)thymine (12).

Full text of DOI:10.1080/07328319608002368

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Nucleosides and Nucleotides
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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
Hiroshi Shiragami a , Yusuke Amino a , Yutaka Honda a , Masayuki
Arai a , Yasuhiro Tanaka a , Hisao Iwagami a , Toshihide Yukawa a
& Kunisuke Izawa a
a Central Research Laboratories, Ajinomoto Co., Inc. , 1-1,
Suzuki-cho, Kawasaki-ku, Kawasaki, 210, Japan
Published online: 21 Aug 2006.
To cite this article: Hiroshi Shiragami , Yusuke Amino , Yutaka Honda , Masayuki Arai , Yasuhiro
Tanaka , Hisao Iwagami , Toshihide Yukawa & Kunisuke Izawa (1996) 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 , Nucleosides and Nucleotides, 15:1-3, 31-45
To link to this article: http://dx.doi.org/10.1080/07328319608002368
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