{[(3aS,4S,7R,7aS)-4-((S)-1-Hydroxy-ethyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ylcarbamoyl]-methyl}-carbamic acid benzyl ester | 175848-49-4

• 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: {[(3aS,4S,7R,7aS)-4-((S)-1-Hydroxy-ethyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ylcarbamoyl]-methyl}-carbamic acid benzyl ester
• CAS: 175848-49-4
• 化学式: C₂₀H₂₆N₂O₈
• 分子量: 422.435
• InChiKey: BXUWBRXAQHUSRD-MDBLMMRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.22
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  132.42
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  {[(3aS,4S,7R,7aS)-4-((S)-1-Hydroxy-ethyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ylcarbamoyl]-methyl}-carbamic acid benzyl ester 在 钯 N-溴代丁二酰亚胺(NBS) 、 氢气 、 sodium acetate 、 三氟乙酸 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 (6R,8S,9R,10R,11R)-9,10,11-Trihydroxy-8-methyl-7-oxa-1,4-diaza-spiro[5.5]undecane-2,5-dione
  参考文献：
  名称：

  Mimics of l-rhamnose: Analogues of rhamnopyranose containing a constituent α-amino acid at the anomeric position. A rhamnopyranose analogue of hydantocidin

  摘要：

  Ionic brominative oxidation of 2-amino derivatives of protected heptonolactones derived from L-rhamnose provides a key bicyclic intermediate for the synthesis of analogues of L-rhamnopyranose with spirohydantoins and spirodiketopiperazines at the anomeric position; the same intermediate can be used for the synthesis of novel glycopeptides containing a constituent rhamnopyranose amino acid. Such materials may allow an approach to new studies of diseases induced by mycobacteria, such as tuberculosis and leprosy.

  DOI：

  10.1016/0957-4166(96)00014-6
• 作为产物：
  描述：

  (3aS,4S,7R,7aS)-7-azido-4-[(1S)-1-hydroxyethyl]-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one 在 钯 吡啶 、 氢气 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 {[(3aS,4S,7R,7aS)-4-((S)-1-Hydroxy-ethyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ylcarbamoyl]-methyl}-carbamic acid benzyl ester
  参考文献：
  名称：

  Mimics of l-rhamnose: Analogues of rhamnopyranose containing a constituent α-amino acid at the anomeric position. A rhamnopyranose analogue of hydantocidin

  摘要：

  Ionic brominative oxidation of 2-amino derivatives of protected heptonolactones derived from L-rhamnose provides a key bicyclic intermediate for the synthesis of analogues of L-rhamnopyranose with spirohydantoins and spirodiketopiperazines at the anomeric position; the same intermediate can be used for the synthesis of novel glycopeptides containing a constituent rhamnopyranose amino acid. Such materials may allow an approach to new studies of diseases induced by mycobacteria, such as tuberculosis and leprosy.

  DOI：

  10.1016/0957-4166(96)00014-6