(1S,2S,6S,7R,11R)-1-Amino-11-hydroxymethyl-4,4-dimethyl-3,5,8,10-tetraoxa-tricyclo[5.2.2.0^2,6]undecan-9-one | 172987-04-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,2S,6S,7R,11R)-1-Amino-11-hydroxymethyl-4,4-dimethyl-3,5,8,10-tetraoxa-tricyclo[5.2.2.0^2,6]undecan-9-one
• CAS: 172987-04-1
• 化学式: C₁₀H₁₅NO₆
• 分子量: 245.232
• InChiKey: DYBYDVUBDXYPLB-GEKCLDMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.52
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  100.24
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  异氰酸苯酯 、 (1S,2S,6S,7R,11R)-1-Amino-11-hydroxymethyl-4,4-dimethyl-3,5,8,10-tetraoxa-tricyclo[5.2.2.0^2,6]undecan-9-one 以21%的产率得到1-((1S,2S,6S,7R,11R)-11-Hydroxymethyl-4,4-dimethyl-9-oxo-3,5,8,10-tetraoxa-tricyclo[5.2.2.0^2,6]undec-1-yl)-3-phenyl-urea
  参考文献：
  名称：

  Spirodiketopiperazines at the anomeric position of mannopyranose: Novel N- linked glycopeptides incorporating an α- amino acid at the anomeric position of mannopyranose

  摘要：

  The first synthesis of a spirodiketopiperazine at the anomeric carbon of a pyranose sugar is described; an N-acylated bicyclic amino [2.2.2] lactone provides access to a new class of glycopeptide analogues of pyranoses and determines the anomeric configuration of the spirodiketopiperazine. The mannopyranose may be equilibrated to the more stable furanose form.

  DOI：

  10.1016/0040-4039(95)01732-w
• 作为产物：
  描述：

  2-azido-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone 在 钯 N-溴代丁二酰亚胺(NBS) 、 水 、 氢气 、 sodium acetate 作用下， 以 溶剂黄146 、 乙酸乙酯 、 乙腈 为溶剂， 生成 (1S,2S,6S,7R,11R)-1-Amino-11-hydroxymethyl-4,4-dimethyl-3,5,8,10-tetraoxa-tricyclo[5.2.2.0^2,6]undecan-9-one
  参考文献：
  名称：

  Spirodiketopiperazines at the anomeric position of mannopyranose: Novel N- linked glycopeptides incorporating an α- amino acid at the anomeric position of mannopyranose

  摘要：

  The first synthesis of a spirodiketopiperazine at the anomeric carbon of a pyranose sugar is described; an N-acylated bicyclic amino [2.2.2] lactone provides access to a new class of glycopeptide analogues of pyranoses and determines the anomeric configuration of the spirodiketopiperazine. The mannopyranose may be equilibrated to the more stable furanose form.

  DOI：

  10.1016/0040-4039(95)01732-w