Synthesis and Use of Glycosyl Phosphites: An Effective Route to Glycosyl Phosphates, Sugar Nucleotides, and Glycosides

Mui Mui Sim; Hirosato Kondo; Chi Huey Wong

doi:10.1021/ja00059a023

Synthesis and Use of Glycosyl Phosphites: An Effective Route to Glycosyl Phosphates, Sugar Nucleotides, and Glycosides

Mui Mui Sim, Hirosato Kondo, Chi Huey Wong

Research output: Contribution to journal › Article

226 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2260-2267
Number of pages	8
Journal	Journal of the American Chemical Society
Volume	115
Issue number	6
DOIs	https://doi.org/10.1021/ja00059a023
Publication status	Published - Mar 1 1993
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja00059a023

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Sim, M. M., Kondo, H., & Wong, C. H. (1993). 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. https://doi.org/10.1021/ja00059a023

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title = "Synthesis and Use of Glycosyl Phosphites: An Effective Route to Glycosyl Phosphates, Sugar Nucleotides, and Glycosides",

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.",

author = "Sim, {Mui Mui} and Hirosato Kondo and Wong, {Chi Huey}",

year = "1993",

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T1 - Synthesis and Use of Glycosyl Phosphites

T2 - An Effective Route to Glycosyl Phosphates, Sugar Nucleotides, and Glycosides

AU - Sim, Mui Mui

AU - Kondo, Hirosato

AU - Wong, Chi Huey

PY - 1993/3/1

Y1 - 1993/3/1

N2 - 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.

AB - 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.

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