Synthesis of 2-Acetamido-2,5-dideoxy-5-phosphoryl-D-glucopyranose Derivatives: New Phospha-sugar Analogs of N-Acetyl-D-glucosamine

• Hanaya, Tadashi

• Kawaguchi, Masahiro

• Sumi, Masakazu

• Makino, Kazuo

• Tsukada, Keiko

• Yamamoto, Hiroshi

抄録

Starting with N-acetyl-D-glucosamine, methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-xylo-hexofuranosid-5-ulose (18) was prepared in 7 steps. The addition reaction of dimethyl phosphonate to 18, followed by deoxygenation of its 5-hydroxy group, provided the 5-deoxy-5-dimethoxyphosphoryl-D-glucofuranoside derivative (21a). The hydride reduction of 21a, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the first D-glucosamine analog (23) having a phosphoryl group in the hemiacetal ring. This was converted into the per-O-acetylated N-acetyl-D-glucosamine phospha-sugar (25), while the same treatment of the 5-deoxy-5-dimethoxyphosphoryl-L-idose dimethyl acetal derivative (13b) afforded the N-acetyl-L-idosamine phospha-sugar (29).

収録刊行物

• Heterocycles

  Heterocycles 86 (2), 1147-1165, 2012-12-31

  Tokyo : Japan Institute of Heterocyclic Chemistry

キーワード

• Phospha-Sugar
• N-Acetyl-D-glucosamine
• Phosphoryl Group
• C-P Bond Formation
• Hetero Sugar

詳細情報

• CRID: 1050846637266107776
• NII論文ID: 120005323825
• NII論文ID: 40019533922
• NII書誌ID: AA00663739
• ISSN: 03855414
• NDL書誌ID: 024170392
• Web Site: https://ousar.lib.okayama-u.ac.jp/51554
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I024170392
• 本文言語コード: en
• 資料種別: journal article
• データソース種別:
  • IRDB
  • NDL
  • CiNii Articles