Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/116615
Title: Synthesis and use of glycosyl phosphites: An effective route to glycosyl phosphates, sugar nucleotides, and glycosides
Authors: Sim, M.M. 
Kondo, H.
Wong, C.-H.
Issue Date: 24-Mar-1993
Source: Sim, M.M.,Kondo, H.,Wong, C.-H. (1993-03-24). Synthesis and use of glycosyl phosphites: An effective route to glycosyl phosphates, sugar nucleotides, and glycosides. Journal of the American Chemical Society 115 (6) : 2260-2267. ScholarBank@NUS Repository.
Abstract: An efficient and convenient synthetic route to glycosyl phosphites and phosphates has been developed that uses dibenzyl N,N-diethylphosphoramidite as a phosphitylating reagent. Glycosyl phosphites and phosphates of 2-acetamido-2-deoxy-D-galactose (GalNAc) (29), 2-acetamido-2-deoxy-D-glucose (GlcNAc) (30), D-galactose (Gal) (31), D-glucose (Glc) (32), D-mannose (Man) (33), L-rhamnose (Rha) (34), L-fucose (Fuc) (35), and N-acetylneuraminic acid (NeuAc) (41) were prepared by this procedure. Compounds 29 and 30 were obtained as α anomers exclusively, whereas compounds 31, 32, and 41 were obtained as β anomers, and compounds 33 and 34, as α anomers, predominately. The phosphates are useful for the synthesis of sugar nucleotides, and the phosphites are effective glycosylation reagents.
Source Title: Journal of the American Chemical Society
URI: http://scholarbank.nus.edu.sg/handle/10635/116615
ISSN: 00027863
Appears in Collections:Staff Publications

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