論文

査読有り 筆頭著者
2012年12月

SYNTHESIS OF 2-ACETAMIDO-2,5-DIDEOXY-5-PHOSPHORYL-D-GLUCOPYRANOSE DERIVATIVES: NEW PHOSPHA-SUGAR ANALOGS OF N-ACETYL-D-GLUCOSAMINE

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

86
2
開始ページ
1147
終了ページ
1165
記述言語
英語
掲載種別
研究論文(学術雑誌)
DOI
10.3987/COM-12-S(N)69
出版者・発行元
PERGAMON-ELSEVIER SCIENCE LTD

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).

リンク情報
DOI
https://doi.org/10.3987/COM-12-S(N)69
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000314390600030&DestApp=WOS_CPL
ID情報
  • DOI : 10.3987/COM-12-S(N)69
  • ISSN : 0385-5414
  • Web of Science ID : WOS:000314390600030

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