Zur Darstellung der Anomeren des Hepta‐O‐acetylcellobiosyl‐, ‐lactosyl‐, ‐maltosyl‐ und ‐melibiosylazids

Csaba Pető, G. Batta, Z. Györgydeák, Ferene Sztaricskai

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37 Citations (Scopus)

Abstract

Synthesis of the Anomers of Hepta‐O‐acetylcellobiosyl, ‐lactosyl, ‐maltosyl, and ‐melibiosyl Azide Synthesis and characterization by 13C‐NMR spectroscopy of the O‐acetylated 1,2‐cis and 1,2‐trans azides of cellobiose, lactose, maltose, and melibiose have been accomplished. 1,2‐trans Azides 1c, 2b–4b result from the stannic chloride catalyzed reaction of the β‐octa‐O‐acetates 1a–4a with trimethylsilyl azide, whereas the β‐chlorohepta‐O‐acetyldisaccharides 1d, 2c–4c afford, in an SN2 reaction in HMPT with lithium azide, the hitherto inaccessible 1,2‐cis azides 1e, 2d–4d.

Original languageGerman
Pages (from-to)505-507
Number of pages3
JournalLiebigs Annalen der Chemie
Volume1991
Issue number5
DOIs
Publication statusPublished - 1991

Keywords

  • Azides
  • Carbohydrates
  • Disaccharides

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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