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
- ,
- ,
- ,
- ,
- ,
- 巻
- 86
- 号
- 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
- ID情報
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- DOI : 10.3987/COM-12-S(N)69
- ISSN : 0385-5414
- Web of Science ID : WOS:000314390600030