Synthesis of C-Glycosyl Phosphate and Phosphonate, Analogues of N-Acetyl-α-d-Glucosamine 1-Phosphate

Synthesis of α-C-ethylene phosphate and phosphonate as well as α-C-methylene phosphate analogues of N-acetyl-α-d-glucosamine 1-phosphate is reported starting from the common perbenzylated 2-acetamido-2-deoxy-α-C-allyl glucoside. Anomerisation of the corresponding amino α-C-glucosyl aldehyde to the β...

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Bibliographic Details
Published in:Journal of carbohydrate chemistry 2003-12, Vol.22 (7-8), p.645-656
Main Authors: Gaurat, Olivier, Xie, Juan, Valéry, Jean-Marc
Format: Article
Language:English
Subjects:
Amino C-glycosides
Glycosyl phosphate
α-C-glucosyl phosphate
α-C-glucosyl phosphonate
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Summary:Synthesis of α-C-ethylene phosphate and phosphonate as well as α-C-methylene phosphate analogues of N-acetyl-α-d-glucosamine 1-phosphate is reported starting from the common perbenzylated 2-acetamido-2-deoxy-α-C-allyl glucoside. Anomerisation of the corresponding amino α-C-glucosyl aldehyde to the β-aldehyde was observed. Thus, both amino α- and β-C-glucosyl methanol were obtained after reduction. † This paper is dedicated to Professor Gérard Descotes on the occasion of his 70th birthday.
ISSN:0732-8303
1532-2327
DOI:10.1081/CAR-120026465