(2S,3S,3aS,4S,5S)-4,5-di-tert-butoxy-2-((R)-1'-benzyloxy-2'-tert-butyldiphenylsilyloxyethyl)-3-(pivaloyloxymethyl)-hexahydropyrrolo[1,2-b]isoxazole | 1122458-12-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,3aS,4S,5S)-4,5-di-tert-butoxy-2-((R)-1'-benzyloxy-2'-tert-butyldiphenylsilyloxyethyl)-3-(pivaloyloxymethyl)-hexahydropyrrolo[1,2-b]isoxazole
• CAS: 1122458-12-1
• 化学式: C₄₅H₆₅NO₇Si
• 分子量: 760.099
• InChiKey: AOMFXNHVLWZODF-FHNMCSBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.72
• 重原子数：
  54.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  75.69
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  2-苄氧基-1-甲基吡啶三氟甲磺酸盐 、 (2S,3S,3aS,4S,5S)-4,5-di-tert-butoxy-2-((R)-2'-tert-butyldiphenylsilyloxy-1'-hydroxyethyl)-3-pivaloyloxymethyl-hexahydropyrrolo[1,2-b]isoxazol 在 magnesium oxide 作用下， 以 苯 为溶剂， 以95%的产率得到(2S,3S,3aS,4S,5S)-4,5-di-tert-butoxy-2-((R)-1'-benzyloxy-2'-tert-butyldiphenylsilyloxyethyl)-3-(pivaloyloxymethyl)-hexahydropyrrolo[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