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Concise Synthesis of P-Glycosyl Alkenylphosphonates and P,C-di and P,P,C tri-Glycosyl Phosphonates
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Concise Synthesis of P-Glycosyl Alkenylphosphonates and P,C-di and P,P,C tri-Glycosyl Phosphonates

Claude Grison et Hicham Chibli
Journal of carbohydrate chemistry, Vol.28(1), pp.12-38
01/01/2009

Résumé

Biochemistry & Molecular Biology Chemistry Chemistry, Organic Life Sciences & Biomedicine Physical Sciences Science & Technology
A direct access to P-glycosyl-, P, P-di-glycosyl alkenylphosphonates and P, C-glycosyl phosphonates is described. The method involves the Horner reaction of an anion derived from P-monoglycosyl and P1, P'-diglycosyl methylenediphosphonates either on the exocyclic aldehyde group of carbohydrates or on the masked aldehydic form of the furanose hemiacetals. In this last case, the carbonyl olefination, followed by an intramolecular cyclization, leads to P,C-di and P,P,C-triglycosyl phosphonates.

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