Facile Approach to 2-Acetamido-2-deoxy-β-d-Glucopyranosides via a Furanosyl Oxazoline

Facile Approach to 2-Acetamido-2-deoxy-β-d-Glucopyranosides via a Furanosyl Oxazoline

A concise and convenient route that may be easily scaled is reported for the preparation of unprotected β-glucopyranosides of N-acetyl-d-glucosamine. Reaction of a wide variety of alcohols with a reactive, readily prepared furanosyl oxazoline under acidic conditions affords the corresponding β-d-glu...

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Veröffentlicht in:Organic letters 2005-09, Vol.7 (18), p.4021-4024
Hauptverfasser: Cai, Ye, Ling, Chang-Chun, Bundle, David R
Format: Artikel
Sprache:eng
Schlagworte:
Combinatorial Chemistry Techniques
Glucosamine - analogs & derivatives
Glucosamine - chemistry
Glucosides - chemical synthesis
Glucosides - chemistry
Glycosylation
Molecular Structure
Oxazoles - chemistry
Stereoisomerism
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Beschreibung
Zusammenfassung:A concise and convenient route that may be easily scaled is reported for the preparation of unprotected β-glucopyranosides of N-acetyl-d-glucosamine. Reaction of a wide variety of alcohols with a reactive, readily prepared furanosyl oxazoline under acidic conditions affords the corresponding β-d-glucopyranosides in good to high yields. Primary alcohols gave only β-d-glucopyranosides. A mechanism is proposed for this transformation.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol051523k