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

J. Kovács, I. Pintér, András Messmer, Gábor Tóth

Research output: Article

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

Fingerprint

Amino Sugars
Carbamates
Sugars
Imides
Carbon Dioxide
Conformations
triphenylphosphine

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Unprotected sugar phosphinimines : A facile route to cyclic carbamates of amino sugars. / Kovács, J.; Pintér, I.; Messmer, András; Tóth, Gábor.

In: Carbohydrate Research, Vol. 141, No. 1, 15.08.1985, p. 57-65.

Research output: Article

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