[(4R,7'S,7'aS)-7'-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-2',4'-dioxospiro[1,3-dioxolane-4,6'-7,7a-dihydro-5H-1-benzofuran]-3'-yl] 2,2-dimethylpropanoate | 616225-43-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: [(4R,7'S,7'aS)-7'-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-2',4'-dioxospiro[1,3-dioxolane-4,6'-7,7a-dihydro-5H-1-benzofuran]-3'-yl] 2,2-dimethylpropanoate
• CAS: 616225-43-5
• 化学式: C₂₃H₃₆O₈Si
• 分子量: 468.62
• InChiKey: VLESTVYGLFCPPD-WSZRMNBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(4R,7'S,7'aS)-7'-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-2',4'-dioxospiro[1,3-dioxolane-4,6'-7,7a-dihydro-5H-1-benzofuran]-3'-yl] 2,2-dimethylpropanoate 在 吡啶 、 copper(l) iodide 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 ammonia borane 、 Rh on carbon 、 碘酰苯 、 二苯基二硒醚 、 硼烷-叔丁基胺 、 氢气 、 sodium methylate 、 四氯化钛 、 对甲苯磺酸 、 三氟乙酸 、 lead(II) chloride 、 锌 、 三甲基乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 氯苯 为溶剂， 100.0~200.0 ℃ 、8.27 MPa 条件下， 反应 2.0h， 生成 (1'R,2'S,4S,6'S,8'R,11'S,12'R)-11'-hydroxy-2,2,4',4'-tetramethyl-12'-prop-2-enylspiro[1,3-dioxolane-4,7'-3,5,9-trioxatricyclo[6.3.1.02,6]dodecane]-10'-one
  参考文献：
  名称：

  A Stereoselective Synthesis of (−)-Tetrodotoxin

  摘要：

  An asymmetric synthesis of the fugu fish poison, (-)-tetrodotoxin, is described. The route to this extraordinary target employs a number of unique transformations, foremost of which are two stereospecific C-H bond functionalization reactions. Accordingly, Rh-catalyzed carbene and nitrene C-H insertions facilitate rapid entry to the cyclohexane core of the natural product and make possible the late-stage installation of the tetrasubstituted carbinolamine center.

  DOI：

  10.1021/ja0368305
• 作为产物：
  描述：

  2,2-Dimethyl-propionic acid (S)-5-[(S)-(tert-butyl-dimethyl-silanyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-4-(2-diazo-acetyl)-2-oxo-2,5-dihydro-furan-3-yl ester 在 Rh₂(HNCOCPh₃)4 作用下， 以 四氯化碳 为溶剂， 生成 [(4R,7'S,7'aS)-7'-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-2',4'-dioxospiro[1,3-dioxolane-4,6'-7,7a-dihydro-5H-1-benzofuran]-3'-yl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  A Stereoselective Synthesis of (−)-Tetrodotoxin

  摘要：

  An asymmetric synthesis of the fugu fish poison, (-)-tetrodotoxin, is described. The route to this extraordinary target employs a number of unique transformations, foremost of which are two stereospecific C-H bond functionalization reactions. Accordingly, Rh-catalyzed carbene and nitrene C-H insertions facilitate rapid entry to the cyclohexane core of the natural product and make possible the late-stage installation of the tetrasubstituted carbinolamine center.

  DOI：

  10.1021/ja0368305

文献信息

• A Stereoselective Synthesis of (−)-Tetrodotoxin
  作者：Andrew Hinman、J. Du Bois

  DOI：10.1021/ja0368305

  日期：2003.9.1

  An asymmetric synthesis of the fugu fish poison, (-)-tetrodotoxin, is described. The route to this extraordinary target employs a number of unique transformations, foremost of which are two stereospecific C-H bond functionalization reactions. Accordingly, Rh-catalyzed carbene and nitrene C-H insertions facilitate rapid entry to the cyclohexane core of the natural product and make possible the late-stage installation of the tetrasubstituted carbinolamine center.