benzyl (3aS,4S,6R,6aR)-4-[(1S)-1-[tert-butyl(dimethyl)silyl]oxybut-3-enyl]-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate | 1186530-60-8

• 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: benzyl (3aS,4S,6R,6aR)-4-[(1S)-1-[tert-butyl(dimethyl)silyl]oxybut-3-enyl]-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• CAS: 1186530-60-8
• 化学式: C₄₂H₅₉NO₆Si₂
• 分子量: 730.105
• InChiKey: YRNNKHHMSBAFMC-GSPXPSQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.44
• 重原子数：
  51
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl (3aS,4S,6R,6aR)-4-[(1S)-1-[tert-butyl(dimethyl)silyl]oxybut-3-enyl]-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 以98%的产率得到
  参考文献：
  名称：

  Total synthesis of the proposed structures of hyacinthacines C2, C3, and their C5-epimers

  摘要：

  Synthesis and structural confirmation of highly oxygenated pyrrolizicline alkaloids, hyacinthacines C-2 [(1S,2R,3R,5R,7S,7aR)-3,5-hydroxymethyl-1,2,7-trihydroxypyrrolizidine], C-3[1S,2R,3R,5S,7R,7aR)-3,5-hydroxymethyl-1,2,7-trihydroxypyrrolizidine], and their C5-epimers were achieved on the basis of the highly divergent method employing (S)-(-)-2-pyrrolidone-5-carboxylic acid as the starting material. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.072
• 作为产物：
  描述：

  benzyl (3aS,4R,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-[(1S)-1-hydroxybut-3-enyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以99%的产率得到benzyl (3aS,4S,6R,6aR)-4-[(1S)-1-[tert-butyl(dimethyl)silyl]oxybut-3-enyl]-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
  参考文献：
  名称：

  Total synthesis of the proposed structures of hyacinthacines C2, C3, and their C5-epimers

  摘要：

  Synthesis and structural confirmation of highly oxygenated pyrrolizicline alkaloids, hyacinthacines C-2 [(1S,2R,3R,5R,7S,7aR)-3,5-hydroxymethyl-1,2,7-trihydroxypyrrolizidine], C-3[1S,2R,3R,5S,7R,7aR)-3,5-hydroxymethyl-1,2,7-trihydroxypyrrolizidine], and their C5-epimers were achieved on the basis of the highly divergent method employing (S)-(-)-2-pyrrolidone-5-carboxylic acid as the starting material. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.072