Highly diastereoselective synthesis of (2'S)-[2'-2H]-2'- deoxyribonucleosides from the corresponding ribonucleosides

Article abstract of DOI:10.1080/15257779508012375

The four (2'S)-[2'-²H]-2'-deoxynucleosides (>90 atom % ²H), were synthesized from the corresponding ribonucleosides involving six steps of reactions, i.e., oxidation of their 2'-hydroxyl group, stereoselective reductive deuteration of the resulting 2'-ketonucleoside intermediates with NaB²H₄ in EtOH-H₂O or EtOH, triflation, bromination with LiBr, highly stereoselective Bu₃SnH-Et₃B reduction of the resulting bromide, and, finally, unmasking.

Full text of DOI:10.1080/15257779508012375

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Nucleosides and Nucleotides
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Highly Diastereoselective Synthesis of
(2′S)-[2′-2H]-2′-Deoxyribonucleosides
from the Corresponding Ribonucleosides
Etsuko Kawashima a , Yukio Aoyama a , Mohamed F. Radwan a
,
Masayoshi Miyahara a , Takeshi Sekine a , Masatsune Kainosho b
Yoshimasa Kyogoku c & Yoshiharu Ishido a
,
a Laboratory of Pharmaceutical Chemistry, Faculty of Pharmacy ,
Tokyo College of Pharmacy , 1432-1, Horinouchi, Hachioji, Tokyo,
192-03, Japan
b Department of Chemistry, Faculty of Science , Tokyo Metropolitan
University , 1-1 Minamiohsawa, Hachioji, Tokyo, 192-03, Japan
c Institute for Protein Research, Osaka University , 3-2
Yamadagaoka, Suita-shi, Osaka, 565, Japan
Published online: 16 Feb 2007.
To cite this article: Etsuko Kawashima , Yukio Aoyama , Mohamed F. Radwan , Masayoshi Miyahara ,
Takeshi Sekine , Masatsune Kainosho , Yoshimasa Kyogoku & Yoshiharu Ishido (1995) Highly
Diastereoselective Synthesis of (2′S)-[2′-2H]-2′-Deoxyribonucleosides from the Corresponding
Ribonucleosides, Nucleosides and Nucleotides, 14:3-5, 333-336
To link to this article: http://dx.doi.org/10.1080/15257779508012375
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