(1R,4S,5R,6R,7R)-4-Azido-5,6,7-trihydroxy-2-oxa-bicyclo[2.2.1]heptan-3-one | 160814-16-4

• 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: (1R,4S,5R,6R,7R)-4-Azido-5,6,7-trihydroxy-2-oxa-bicyclo[2.2.1]heptan-3-one
• 英文别名: (1R,4S,5R,6R,7R)-4-azido-5,6,7-trihydroxy-2-oxabicyclo[2.2.1]heptan-3-one
• CAS: 160814-16-4
• 化学式: C₆H₇N₃O₅
• 分子量: 201.139
• InChiKey: CGILELFMZVTEIU-BYHBOUFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R,4S,5R,6R,7R)-4-Azido-5,6,7-trihydroxy-2-oxa-bicyclo[2.2.1]heptan-3-one 在 sodium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以94%的产率得到(1R,4R,5S,6R,7R)-1-azido-5,6,7-trihydroxy-2-oxabicyclo<2.2.1>heptan-3-one
  参考文献：
  名称：

  Aldol equilibrations of unprotected trihydroxybicyclic lactones: Enantiomeric tetrahydroxy-α-aminocyclopentane carboxylic acids from epimeric bicyclic lactones

  摘要：

  Six stereoisomers - including an enantiomeric pair - of 1-amino-2,3,4,5-tetrahydroxy-cyclopentane-1-carboxylate have been prepared from a single azidolactone starting material by a series of remarkable aldol equilibrations.

  DOI：

  10.1016/s0040-4039(00)78528-5
• 作为产物：
  描述：

  (1R,2R,6R,7R,10R)-1-Azido-10-hydroxy-4,4-dimethyl-3,5,8-trioxa-tricyclo[5.2.1.0^2,6]decan-9-one 在 三氟乙酸 作用下， 以 水 为溶剂， 以89%的产率得到(1R,4S,5R,6R,7R)-4-Azido-5,6,7-trihydroxy-2-oxa-bicyclo[2.2.1]heptan-3-one
  参考文献：
  名称：

  Polyhydroxylated cyclohexane and cyclopentane α-amino acids from cyclisations of an azidolactone

  摘要：

  Short routes to tetrahydroxylated cyclohexane and cyclopentane alpha-amino acids with control of the stereochemistry at all 5 carbons bearing functional groups are described from an azidolactone.

  DOI：

  10.1016/s0040-4039(00)78527-3