(3S,5R)-N-methoxy-N-methyl-3,5-bis(tert-butyldimethylsilanyloxy)-7-iodo-5,6-dimethylhept-6-ynoic amide | 874674-61-0

• 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: (3S,5R)-N-methoxy-N-methyl-3,5-bis(tert-butyldimethylsilanyloxy)-7-iodo-5,6-dimethylhept-6-ynoic amide
• 英文别名: (E,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-7-iodo-N-methoxy-N,5,6-trimethylhept-6-enamide
• CAS: 874674-61-0
• 化学式: C₂₃H₄₈INO₄Si₂
• 分子量: 585.714
• InChiKey: WCIGWXUGLHRXOW-JIIHZUQJSA-N

物化性质

• 沸点：
  492.8±55.0 °C(predicted)
• 密度：
  1.135±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,5R)-2-(1-{3-[3-(tert-butyldimethylmethylsilanyloxymethyl)oxiranyl]-2-methylpropyl}vinyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 、 (3S,5R)-N-methoxy-N-methyl-3,5-bis(tert-butyldimethylsilanyloxy)-7-iodo-5,6-dimethylhept-6-ynoic amide 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 barium dihydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以80%的产率得到(E)-(3S,5R,10R)-N-methoxy-N-methyl-3,5-bis(tert-butyldimethylmethylsilanyloxy)-11-[(2S,3S)-3-(tert-butyldimethylsilanyloxymethyl)oxiranyl]-5,6,10-trimethyl-8-methyleneundec-6-enoic amide
  参考文献：
  名称：

  Amphidinolide B:  Asymmetric Synthesis of a C₇−C₂₀ Synthon

  摘要：

  An asymmetric synthesis of a C-7-C-20 synthon of amphidinolide B is described. The synthesis entails the construction of C-7-C-13 and C-14-C-20 fragments and makes extensive use of catalytic asymmetric bond constructions to establish the requisite stereochemical relationships. Fragment coupling proceeds by Suzuki cross-coupling and installs the trisubstituted diene unit that is among amphidinolide B's defining structural features.

  DOI：

  10.1021/ol051861l
• 作为产物：
  描述：

  (3S,5R)-N-methoxy-N-methyl-3,5-bis(tert-butyldimethylsilanyloxy)-5,6-dimethyl-7-tributylstannylhept-6-ynoic amide 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以98%的产率得到(3S,5R)-N-methoxy-N-methyl-3,5-bis(tert-butyldimethylsilanyloxy)-7-iodo-5,6-dimethylhept-6-ynoic amide
  参考文献：
  名称：

  Amphidinolide B:  Asymmetric Synthesis of a C₇−C₂₀ Synthon

  摘要：

  An asymmetric synthesis of a C-7-C-20 synthon of amphidinolide B is described. The synthesis entails the construction of C-7-C-13 and C-14-C-20 fragments and makes extensive use of catalytic asymmetric bond constructions to establish the requisite stereochemical relationships. Fragment coupling proceeds by Suzuki cross-coupling and installs the trisubstituted diene unit that is among amphidinolide B's defining structural features.

  DOI：

  10.1021/ol051861l