Synthesis of glycosyl chlorides using catalytic Appel conditions

Organic & Biomolecular Chemistry
Imlirenla PongenerEoghan M McGarrigle

Abstract

The stereoselective synthesis of glycosyl chlorides using catalytic Appel conditions is described. Good yields of α-glycosyl chlorides were obtained using a range of glycosyl hemiacetals, oxalyl chloride and 5 mol% Ph3PO. For 2-deoxysugars treatment of the corresponding hemiacetals with oxalyl chloride without phosphine oxide catalyst also gave good yields of glycosyl chloride. The method is operationaly simple and the 5 mol% phosphine oxide by-product can be removed easily. Alternatively a one-pot, multi-catalyst glycosylation can be carried out to transform the glycosyl hemiacetal directly to a glycoside.

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Citations

Jun 26, 2020·Organic & Biomolecular Chemistry·Serena TraboniAlfonso Iadonisi
Jan 20, 2021·Journal of the American Chemical Society·Jeffrey M LipshultzAlexander T Radosevich

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Methods Mentioned

BETA
1
H
NMR
X-ray
glycosylation

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