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Synlett 2005(14): 2242-2244  
DOI: 10.1055/s-2005-872244
LETTER
© Georg Thieme Verlag Stuttgart · New York

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;
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Publication History

Received 10 June 2005
Publication Date:
26 July 2005 (online)

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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