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Neighbouring acetamido-group participation in reactions of derivatives of 2-acetamido-2-deoxy-D-glucose.

Authors
  • Ballardie, F W
  • Capon, B
  • Dearie, W M
  • Foster, R L
Type
Published Article
Journal
Carbohydrate Research
Publisher
Elsevier
Publication Date
Jul 01, 1976
Volume
49
Pages
79–92
Identifiers
PMID: 963707
Source
Medline
License
Unknown

Abstract

Kinetic measurements suggest that neighbouring acetamido-group participation occurs in the spontaneous hydrolysis and methanolysis of o-carboxyphenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside and in the spontaneous hydrolysis of 2,4-dinitrophenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside and 2-acetamido-2-deoxy-beta-D-glycopyranosyl fluoride. The methanolyses of these compounds proceed with predominant retention of configuration which is also consistent with neighbouring acetamido-group participation. The oxazoline intermediate which would arise from such a process was detected during methanolysis of 2-acetamido-2-deoxy-beta-D-glucopyranosyl fluoride in the presence of bases by n.m.r., i.r., and u.v. spectroscopy. Attempts to isolate the oxazoline were unsuccessful.

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