1,2-trans-Glycosyl Azides of Sugar 2-Sulfonic Acids

László Lázár; István Bajza; Zsolt Jakab; András Lipták

doi:10.1055/s-2005-872244

LETTER

1,2-trans-Glycosyl Azides of Sugar 2-Sulfonic Acids

László Lázár, István Bajza, Zsolt Jakab, András Lipták*
Research Group for Carbohydrates of the Hungarian Academy of Sciences, P.O. Box 55, 4010 Debrecen, Hungary
Fax: +36(52)512913; e-Mail: liptaka@puma.unideb.hu;

Abstract

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Abstract

Treatment of the 2-O-mesylated 1-SAc-, 1-S[2-(trimethylsilyl)ethyl]-α-d-manno-, and 1-SAll-β-d-gluco-pyranosides with NaN₃ resulted exclusively in 2-SAc-, 2-S[2-(trimethylsilyl)ethyl]-β-d-gluco-, and 2-SAll-α-manno-pyranosyl azides. The 2-S substituents were removed either with acetic acid (SAc), or Hg(TFA)₂ (SCH₂CH₂SiMe₃, SCH=CHCH₃) and the 2-SH groups were oxidized into sugar 2-sulfonic acids giving 1,2-trans-glycosyl azides.

Key words

1,2-thio-migration - 2-S substituents - glycosyl azides - sugar 2-sulfonic acids

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