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

Mui Mui Sim, Hirosato Kondo, Chi Huey Wong

研究成果: Contribution to journalArticle査読

226 被引用数 (Scopus)

抄録

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.

本文言語英語
ページ(範囲)2260-2267
ページ数8
ジャーナルJournal of the American Chemical Society
115
6
DOI
出版ステータス出版済み - 3 1 1993
外部発表はい

All Science Journal Classification (ASJC) codes

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

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