The use of N-alkoxycarbonyl derivatives of 2-amino-2-deoxy- d-glucose as donors in glycosylation reactions

1,3,4,6-Tetra- O-acetyl-2-alkoxycarbonylamino-2-deoxy-β- d-glucopyranoses and 3,4,6-tri- O-acetyl-2-alkoxycarbonylamino-2-deoxy- a- d-glucopyranosyl bromides have been used as donors in glycosylation reactions with model alcohols. β-Glycosides were obtained in good yields and with a high degree of 1...

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Bibliographic Details
Published in:Carbohydrate research 1990-07, Vol.202, p.151-164
Main Authors: Boullanger, Paul, Jouineau, Martine, Bouammali, Boufelja, Lafont, Dominique, Descotes, Gérard
Format: Article
Language:English
Subjects:
Alcohols
Carbohydrate Sequence
Chemical Phenomena
Chemistry
Glucosamine - analogs & derivatives
Glucosamine - chemical synthesis
Glycosylation
Magnetic Resonance Spectroscopy
Molecular Sequence Data
Molecular Structure
Oligosaccharides - chemical synthesis
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Summary:1,3,4,6-Tetra- O-acetyl-2-alkoxycarbonylamino-2-deoxy-β- d-glucopyranoses and 3,4,6-tri- O-acetyl-2-alkoxycarbonylamino-2-deoxy- a- d-glucopyranosyl bromides have been used as donors in glycosylation reactions with model alcohols. β-Glycosides were obtained in good yields and with a high degree of 1,2- trans stereoselectivity. An oxazolidinone was formed as the main product from the reaction of some of the glucopyranosyl bromides with alcohols of low reactivity, but the formation of all products could be interpreted by a strong participation of the alkoxycarbonylamino group.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(90)84077-8