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 journalArticle

221 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 languageEnglish
Pages (from-to)2260-2267
Number of pages8
JournalJournal of the American Chemical Society
Volume115
Issue number6
DOIs
Publication statusPublished - Mar 1 1993
Externally publishedYes

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Sugar Phosphates
Phosphites
Glycosides
Nucleotides
Phosphates
Glucose
Glycosylation
Acetylgalactosamine
Rhamnose
Fucose
Acetylglucosamine
N-Acetylneuraminic Acid
Mannose
Galactose
Sugars
Acids

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Synthesis and Use of Glycosyl Phosphites : An Effective Route to Glycosyl Phosphates, Sugar Nucleotides, and Glycosides. / Sim, Mui Mui; Kondo, Hirosato; Wong, Chi Huey.

In: Journal of the American Chemical Society, Vol. 115, No. 6, 01.03.1993, p. 2260-2267.

Research output: Contribution to journalArticle

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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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