Volume 31, Issue 7
Natural Products
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ChemInform Abstract: Efficient Electrochemical N-Glycosylation of Silylated Pyrimidines with Protected Arylthioriboses in the Presence of a Catalytic Amount of NBS or Br2.

Junzo Nokami

Junzo Nokami

Dep. Appl. Chem., Okayama Univ. Sci., Ridai, Okayama 700, Japan

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Masahiro Osafune

Masahiro Osafune

Dep. Appl. Chem., Okayama Univ. Sci., Ridai, Okayama 700, Japan

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Yuichiro Ito

Yuichiro Ito

Dep. Appl. Chem., Okayama Univ. Sci., Ridai, Okayama 700, Japan

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Fumiaki Miyake

Fumiaki Miyake

Dep. Appl. Chem., Okayama Univ. Sci., Ridai, Okayama 700, Japan

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Shin-ichi Sumida

Shin-ichi Sumida

Dep. Appl. Chem., Okayama Univ. Sci., Ridai, Okayama 700, Japan

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Sigeru Torii

Sigeru Torii

Dep. Appl. Chem., Okayama Univ. Sci., Ridai, Okayama 700, Japan

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First published: 10 June 2010

Abstract

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ChemInform Abstract

Electrolysis of silylated pyrimidines (II) with protected arylthioribose (I) in the presence of a catalytic amount of NBS or Br2 as mediator gives the corresponding nucleosides in good yields. The stereoselectivity of this glycosylation is similar to that of chemical glycosylation using a stoichiometric amount of NBS.

chemical structure image

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