(3aS,4S,7R,7aS)-7-Amino-4-((S)-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one | 175848-43-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3aS,4S,7R,7aS)-7-Amino-4-((S)-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one
• CAS: 175848-43-8
• 化学式: C₁₀H₁₇NO₅
• 分子量: 231.249
• InChiKey: RRVBFCXFLFQBJM-GWVFRZDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.86
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  91.01
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3aS,4S,7R,7aS)-7-Amino-4-((S)-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 sodium acetate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 1-Phenyl-3-((1R,2R,6R,7S,11S)-4,4,11-trimethyl-9-oxo-3,5,8,10-tetraoxa-tricyclo[5.2.2.0^2,6]undec-1-yl)-urea
  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 氢气 作用下， 以 乙醇 为溶剂， 以90%的产率得到(3aS,4S,7R,7aS)-7-Amino-4-((S)-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one
  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