Unprotected sugar phosphinimines: A facile route to cyclic carbamates of amino sugars

József Kovács, István Pintér, András Messmer, Gábor Tóth

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64 Citations (Scopus)

Abstract

Unprotected sugar phosphinimines were prepared from various azido sugars by reaction with triphenylphosphine and were converted by carbon dioxide into cyclic carbamates of amino sugars. The reaction could be carried out more conveniently in a one-pot process without isolation of the phosphinimines. The 13C-and 31P-n.m.r. data for N-(β-d-glucopyranosyl)triphenylphosphine imide (2) revealed an unexpected conformation of the phosphinimine moiety (proposed as a "reverse exo-anomeric effect") stabilised by an interaction with HO-2.

Original languageEnglish
Pages (from-to)57-65
Number of pages9
JournalCarbohydrate Research
Volume141
Issue number1
DOIs
Publication statusPublished - Aug 15 1985

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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