(R)-1-((2S,3S,3aS,4S,5S)-4,5-di-tert-butoxy-3-(tert-butyldiphenylsilyloxymethyl)-hexahydropyrrolo[1,2-b]isoxazol-2-yl)ethyl mesylate | 1122458-41-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (R)-1-((2S,3S,3aS,4S,5S)-4,5-di-tert-butoxy-3-(tert-butyldiphenylsilyloxymethyl)-hexahydropyrrolo[1,2-b]isoxazol-2-yl)ethyl mesylate
• CAS: 1122458-41-6
• 化学式: C₃₄H₅₃NO₇SSi
• 分子量: 647.949
• InChiKey: SAKRVATVERRXOK-HZXQWRGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  44.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  83.53
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (R)-1-((2S,3S,3aS,4S,5S)-4,5-di-tert-butoxy-3-(tert-butyldiphenylsilyloxymethyl)-hexahydropyrrolo[1,2-b]isoxazol-2-yl)ethyl mesylate 在 10% Pd/C 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以93%的产率得到(1S,2S,3S,6S,7S,7aS)-6,7-di-tert-butoxy-1-(tert-butyldiphenylsilyloxymethyl)-2-hydroxy-3-methyl-pyrrolizidine
  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：

  (R)-1-((2S,3S,3aS,4S,5S)-4,5-di-tert-butoxy-3-(tert-butyldiphenylsilyloxymethyl)-hexahydropyrrolo[1,2-b]isoxazol-2-yl)ethanol 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(R)-1-((2S,3S,3aS,4S,5S)-4,5-di-tert-butoxy-3-(tert-butyldiphenylsilyloxymethyl)-hexahydropyrrolo[1,2-b]isoxazol-2-yl)ethyl mesylate
  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