A 13C-N.M.R. investigation of glycosyl azides and other azido sugars: Stereochemical influences on the one-bond 13C-1H coupling constants

László Szilágyi, Zoltán Györgydeák

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74 Citations (Scopus)

Abstract

Unambiguous 13C assignments have been obtained, using 2D-n.m.r. techniques, for several glycosyl azides, 6-deoxyglycosyl azides, 2-acylamino-2-deoxyglycosyl azides, and some 2- and 3-azido monosaccharide derivatives. For non-anomeric CH bonds the 1JC,He values are 4-9 Hz larger than the 1JC,Ha values. A substituent (hydroxyl, acetoxyl, alkoxyl, azido, etc.) in 1,3-diaxial relationship with Ha significantly increases the value of 1JC,Ha. Bond-angle distortions in the fused-ring bicyclic systems of some isopropylidene derivatives result in 1JC,Ha values being larger than 1JC,He values. Electronic and steric effects of substituents at non-anomeric carbons may alter the 1JC,H values for anomeric carbons to such an extent that they may no longer be useful for diagnosing anomeric configuration. Bond-angle deformations also influence the 13C chemical shift differences in α- and β-anomers at C-5 and, to a lesser extent, at C-3.

Original languageEnglish
Pages (from-to)21-41
Number of pages21
JournalCarbohydrate Research
Volume143
Issue numberC
DOIs
Publication statusPublished - Nov 1 1985

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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