(3aR,4S,6S,6aR)-4-(2-Benzyloxycarbonylamino-acetylamino)-6-((S)-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester | 176198-60-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3aR,4S,6S,6aR)-4-(2-Benzyloxycarbonylamino-acetylamino)-6-((S)-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester
• CAS: 176198-60-0
• 化学式: C₂₁H₂₈N₂O₉
• 分子量: 452.461
• InChiKey: GOCSCLREUAGYLR-XNFFJXRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  141.65
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (3aR,4S,6S,6aR)-4-(2-Benzyloxycarbonylamino-acetylamino)-6-((S)-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester 在 钯 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 72.0h， 生成 (3aR,4S,6S,6aR)-6-((S)-1-hydroxyethyl)-2,2-dimethyldihydro-6H-spiro[furo[3,4-d][1,3]dioxole-4,2'-piperazine]-3',6'-dione
  参考文献：
  名称：

  Mimics of l-rhamnose: Anomeric spirohydantoins and diketopiperazines-approaches to novel N-linked glycopeptides of rhamnofuranose

  摘要：

  An alpha-azidocarboxylate of a tetrahydrofuran derived from L-rhamnose may be used as a divergent intermediate for a wide range of mimics of L-rhamnofuranose, which contain a constituent alpha-amino acid moiety at the anomeric position, and include anomeric spiroderivatives such as the rhamnose analogue of hydantocidin; such materials may be helpful in elucidating the biosynthesis of the cells walls of mycobacteria.

  DOI：

  10.1016/0957-4166(96)00013-4
• 作为产物：
  描述：

  (3aR,4R,6S,6aR)-4-Azido-6-((S)-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester 在 钯 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3aR,4S,6S,6aR)-4-(2-Benzyloxycarbonylamino-acetylamino)-6-((S)-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Mimics of l-rhamnose: Anomeric spirohydantoins and diketopiperazines-approaches to novel N-linked glycopeptides of rhamnofuranose

  摘要：

  An alpha-azidocarboxylate of a tetrahydrofuran derived from L-rhamnose may be used as a divergent intermediate for a wide range of mimics of L-rhamnofuranose, which contain a constituent alpha-amino acid moiety at the anomeric position, and include anomeric spiroderivatives such as the rhamnose analogue of hydantocidin; such materials may be helpful in elucidating the biosynthesis of the cells walls of mycobacteria.

  DOI：

  10.1016/0957-4166(96)00013-4