7772-87-4Relevant articles and documents
Synthesis of glycosyl chlorides using catalytic Appel conditions
Pongener, Imlirenla,Nikitin, Kirill,McGarrigle, Eoghan M.
supporting information, p. 7531 - 7535 (2019/08/20)
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.
A facile and stereoselective synthesis of 3,4,6-tri-O-acetyl-2-deoxy-2- phthalimido-β-D-glucopyranosyl chloride
Cao, Zhiling,Liu, Wenjie,Qu, Yingying,Yao, Guowei,Gao, Dachao,Liu, Weiwei
, p. 467 - 469 (2013/09/12)
Acetylation of D-glucosamine catalysed by sulfuric acid and N-phthaloylation of the glucosyl acetate yielded 1,3,4,6- tetra-O-acetyl-2- deoxy-2-phthalimido-α-D-glucopyranose. This gave the corresponding pure β-glucosyl chloride upon treatment with PCl5-BF3. An anomeric chlorination with thionyl chloride combined with the Lewis acids (ZnCl2, SnCl4 and BiCl3) resulted in an α/β anomer mixture.
A convenient preparation of glycosyl chlorides from aryl/alkyl thioglycosides
Sugiyama, Shin,Diakur, James M.
, p. 2713 - 2715 (2007/10/03)
(equation presented) Because of the vast structural diversity encountered in the field of glycobiology, versatile methods for orthogonal oligosaccharide assembly are always of interest. Reported herein is the preparation of glycosyl chloride donors obtained by reaction of the corresponding thioglycoside precursors with chlorosulfonium chloride reagent 4. The crude chlorides thus obtained can be used directly in subsequent glycosylation reactions, and examples of the generality of this approach are provided.