benzyl (2-(((3a'R,4'R,6'S,7'S,7a'R)-6'-methyl-9'-oxotetrahydro-4'H-spiro[cyclohexane-1,2'-[7,4](epoxymethano)[1,3]dioxolo[4,5-c]pyran]-4'-yl)amino)-2-oxoethyl)carbamate | 175848-52-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: benzyl (2-(((3a'R,4'R,6'S,7'S,7a'R)-6'-methyl-9'-oxotetrahydro-4'H-spiro[cyclohexane-1,2'-[7,4](epoxymethano)[1,3]dioxolo[4,5-c]pyran]-4'-yl)amino)-2-oxoethyl)carbamate
• CAS: 175848-52-9
• 化学式: C₂₃H₂₈N₂O₈
• 分子量: 460.484
• InChiKey: HJCWXQRRXVILTN-ASUQADSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  121.42
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  benzyl (2-(((3a'R,4'R,6'S,7'S,7a'R)-6'-methyl-9'-oxotetrahydro-4'H-spiro[cyclohexane-1,2'-[7,4](epoxymethano)[1,3]dioxolo[4,5-c]pyran]-4'-yl)amino)-2-oxoethyl)carbamate 在 钯 氢气 、 三氟乙酸 作用下， 以 乙醇 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：

  (3a'S,4'S,7'R,7a'S)-7'-azido-4'-((S)-1-hydroxyethyl)tetrahydro-6'H-spiro[cyclohexane-1,2'-[1,3]dioxolo[4,5-c]pyran]-6'-one 在 钯 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 氢气 、 sodium acetate 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 benzyl (2-(((3a'R,4'R,6'S,7'S,7a'R)-6'-methyl-9'-oxotetrahydro-4'H-spiro[cyclohexane-1,2'-[7,4](epoxymethano)[1,3]dioxolo[4,5-c]pyran]-4'-yl)amino)-2-oxoethyl)carbamate
  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