(1aS,2R,6aS,6bS,7S,8S)-7,8-di-tert-butoxy-2,3,3-trimethyloctahydro[1,3]dioxepino[5,6-d]pyrrolo[1,2-b]isoxazole | 1122458-35-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (1aS,2R,6aS,6bS,7S,8S)-7,8-di-tert-butoxy-2,3,3-trimethyloctahydro[1,3]dioxepino[5,6-d]pyrrolo[1,2-b]isoxazole
• CAS: 1122458-35-8
• 化学式: C₂₀H₃₇NO₅
• 分子量: 371.517
• InChiKey: ZULXQAYXZJZQSX-KOWPAETKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.39
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1aS,2R,6aS,6bS,7S,8S)-7,8-di-tert-butoxy-2,3,3-trimethyloctahydro[1,3]dioxepino[5,6-d]pyrrolo[1,2-b]isoxazole 在 对甲苯磺酸 作用下， 以 甲醇 、 水 为溶剂， 以80%的产率得到(R)-1-((2S,3S,3aS,4S,5S)-4,5-di-tert-butoxy-3-(hydroxymethyl)-hexahydropyrrolo[1,2-b]isoxazol-2-yl)ethanol
  参考文献：
  名称：

  Synthesis of casuarine-related derivatives via 1,3-dipolar cycloaddition between a cyclic nitrone and an unsaturated γ-lactone

  摘要：

  The 1,3-dipolar cycloaddition of the cyclic nitrone derived from tartaric acid and (S)-5-hydroxymethyl-2(5H)-furanone leads to the single adduct 7 which can be transformed into the 3-epi-1-homo-casuarine via a reaction sequence involving reduction of the lactone moiety and N-O bond hydrogenolysis, followed by intramolecular alkylation of the nitrogen atom. The adduct 7 can also be used in the synthesis of 1-methyl- or 3-methyl analogues of 3-epi-casuarine. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.10.016
• 作为产物：
  描述：

  (1aS,2R,6aS,6bS,7S,8S)-7,8-di(tert-butoxy)-2-(mesyloxymethyl)-3,3-dimethyl-octahydro-[1,3]dioxepino[5,6-d]pyrrolo[1,2-b]isoxazole 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到(1aS,2R,6aS,6bS,7S,8S)-7,8-di-tert-butoxy-2,3,3-trimethyloctahydro[1,3]dioxepino[5,6-d]pyrrolo[1,2-b]isoxazole
  参考文献：
  名称：

  Synthesis of casuarine-related derivatives via 1,3-dipolar cycloaddition between a cyclic nitrone and an unsaturated γ-lactone

  摘要：

  The 1,3-dipolar cycloaddition of the cyclic nitrone derived from tartaric acid and (S)-5-hydroxymethyl-2(5H)-furanone leads to the single adduct 7 which can be transformed into the 3-epi-1-homo-casuarine via a reaction sequence involving reduction of the lactone moiety and N-O bond hydrogenolysis, followed by intramolecular alkylation of the nitrogen atom. The adduct 7 can also be used in the synthesis of 1-methyl- or 3-methyl analogues of 3-epi-casuarine. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.10.016