Synthesis of 2-acetamido-2,5-dideoxy-5-phosphoryl-dglucopyranose derivatives: New phospha-sugar analogs of N-acetyl-D-glucosamine

Tadashi Hanaya, Masahiro Kawaguchi, Masakazu Sumi, Kazuo Makino, Keiko Tsukada, Hiroshi Yamamoto

Research output: Contribution to journalArticle

Abstract

Starting with N-acetyl-D-glucosamine, methyl 2-acetamido-3,6-di-Obenzyl- 2-deoxy-β-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-Dglucofuranoside 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).

Original languageEnglish
Pages (from-to)1147-1165
Number of pages19
JournalHeterocycles
Volume86
Issue number2
DOIs
Publication statusPublished - 2012

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Acetylglucosamine
Sugars
Derivatives
Addition reactions
Hydrochloric Acid
Glucosamine
Hydrides
Hydrogen Peroxide
idose
dimethyl hydrogen phosphite
1,1-dimethoxyethane

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

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Synthesis of 2-acetamido-2,5-dideoxy-5-phosphoryl-dglucopyranose derivatives : New phospha-sugar analogs of N-acetyl-D-glucosamine. / Hanaya, Tadashi; Kawaguchi, Masahiro; Sumi, Masakazu; Makino, Kazuo; Tsukada, Keiko; Yamamoto, Hiroshi.

In: Heterocycles, Vol. 86, No. 2, 2012, p. 1147-1165.

Research output: Contribution to journalArticle

Hanaya, Tadashi ; Kawaguchi, Masahiro ; Sumi, Masakazu ; Makino, Kazuo ; Tsukada, Keiko ; Yamamoto, Hiroshi. / Synthesis of 2-acetamido-2,5-dideoxy-5-phosphoryl-dglucopyranose derivatives : New phospha-sugar analogs of N-acetyl-D-glucosamine. In: Heterocycles. 2012 ; Vol. 86, No. 2. pp. 1147-1165.
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abstract = "Starting with N-acetyl-D-glucosamine, methyl 2-acetamido-3,6-di-Obenzyl- 2-deoxy-β-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-Dglucofuranoside 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).",
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