(3a'S,4'S,7'R,7a'S)-7'-amino-4'-((S)-1-hydroxyethyl)tetrahydro-6'H-spiro[cyclohexane-1,2'-[1,3]dioxolo[4,5-c]pyran]-6'-one | 175848-44-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3a'S,4'S,7'R,7a'S)-7'-amino-4'-((S)-1-hydroxyethyl)tetrahydro-6'H-spiro[cyclohexane-1,2'-[1,3]dioxolo[4,5-c]pyran]-6'-one
• CAS: 175848-44-9
• 化学式: C₁₃H₂₁NO₅
• 分子量: 271.313
• InChiKey: ZILXDWPZBUKHDG-HPENLJRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.06
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  (3a'S,4'S,7'R,7a'S)-7'-amino-4'-((S)-1-hydroxyethyl)tetrahydro-6'H-spiro[cyclohexane-1,2'-[1,3]dioxolo[4,5-c]pyran]-6'-one 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 sodium acetate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 {[(2R,3R,4R,5R,6S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-carbonyl]-amino}-acetic acid methyl 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
• 作为产物：
  描述：

  3,4-O-cyclohexylidene-7-deoxy-L-glycero-L-talo-heptono-1,5-lactone 在 钯 吡啶 、 sodium azide 、 氢气 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3a'S,4'S,7'R,7a'S)-7'-amino-4'-((S)-1-hydroxyethyl)tetrahydro-6'H-spiro[cyclohexane-1,2'-[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