M. Sim, H. Kondo, Chi‐Huey Wong
Mar 1, 1993
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0
Influential Citations
171
Citations
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Journal
Journal of the American Chemical Society
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) (38), 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 β-anomers, ands 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