An Exceptionally Simple Chemical Synthesis of O-Glycosylated d-Glucosamine Derivatives by Heyns Rearrangement of the Corresponding O-Glycosyl Fructoses 1

2-N-Acetyl-4-O-( beta -d-galactopyranosyl)-d-glucosamine (N-acetyl-d-lactosamine), a very important building block of biologically relevant oligosaccharides such as sialyl Lewisx, is easily accessible via the Heyns rearrangement of the corresponding O-glycosylated ketohexose, d-lactulose. This appro...

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Bibliographic Details
Published in:Journal of carbohydrate chemistry 2003-01, Vol.22 (5), p.253-265
Main Authors: Stutz, Arnold E, Dekany, Gyula, Eder, Brigitte, Illaszewicz, Carina, Wrodnigg, Tanja M
Format: Article
Language:English
Online Access:Get full text
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Summary:2-N-Acetyl-4-O-( beta -d-galactopyranosyl)-d-glucosamine (N-acetyl-d-lactosamine), a very important building block of biologically relevant oligosaccharides such as sialyl Lewisx, is easily accessible via the Heyns rearrangement of the corresponding O-glycosylated ketohexose, d-lactulose. This approach can also be extended to other glucosamine derivatives employing suitable O-glycosylated ketoses many of which are commercially available. For example, nigerosamine (3-O-a-d-glucopyranosyl-d-glucosamine) was prepared from turanose (3-O-a-d-glucopyranosyl-d-fructose). In combination with a recently introduced vinylogous amide type N-protecting group, [1,3-dimethyl-2, 4, 6 (1H, 3H, 5H)-trioxopyrimidine-5-ylidene] methyl (DTPM), this access is clearly superior to other routes and eminently suitable for scaling up.
ISSN:0732-8303
DOI:10.1081/CAR-120023468