(4E,6E,8S,9R,10E,12S,13R,14S,16S,17R)-9-(tert-Butyldimethylsiloxy)-13,14,17,20,22-pentamethoxy-4,8,10,12,16-pentamethyl-2-azabicyclo<16.3.1>docosa-1(22),4,6,10,18,20-hexaen-3-one | 123083-99-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (4E,6E,8S,9R,10E,12S,13R,14S,16S,17R)-9-(tert-Butyldimethylsiloxy)-13,14,17,20,22-pentamethoxy-4,8,10,12,16-pentamethyl-2-azabicyclo<16.3.1>docosa-1(22),4,6,10,18,20-hexaen-3-one
• 英文别名: (4E,6E,8S,9R,10E,12S,13R,14S,16S,17R)-9-(tert-Butyldimethylsiloxy)-13,14,17,20,22-pentamethoxy-4,8,10,12,16-pentamethyl-2-azabicyclo[16.3.1]docosa-1(22),4,6,10,18,20-hexaen-3-one；(4E,6E,8S,9R,10E,12S,13R,14S,16S,17R)-9-[tert-butyl(dimethyl)silyl]oxy-13,14,17,20,22-pentamethoxy-4,8,10,12,16-pentamethyl-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-3-one
• CAS: 123083-99-8；145551-73-1
• 化学式: C₃₇H₆₁NO₇Si
• 分子量: 659.979
• InChiKey: WCXQVMOYIFJQSL-HYGOYTDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.51
• 重原子数：
  46
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4E,6E,8S,9R,10E,12S,13R,14S,16S,17R)-9-(tert-Butyldimethylsiloxy)-13,14,17,20,22-pentamethoxy-4,8,10,12,16-pentamethyl-2-azabicyclo<16.3.1>docosa-1(22),4,6,10,18,20-hexaen-3-one 、 四丁基氟化铵 以89%的产率得到
  参考文献：
  名称：

  BAKER, RAYMOND;CASTRO, JOSE L., J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 47-65

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (E)-4-dichlorophosphoryl-2-methylbut-2-enoate 在 Lindlar's catalyst 喹啉 、 lithium hydroxide 、 正丁基锂 、 氢气 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 甲苯 、 苯 为溶剂， 反应 72.5h， 生成 (4E,6E,8S,9R,10E,12S,13R,14S,16S,17R)-9-(tert-Butyldimethylsiloxy)-13,14,17,20,22-pentamethoxy-4,8,10,12,16-pentamethyl-2-azabicyclo<16.3.1>docosa-1(22),4,6,10,18,20-hexaen-3-one
  参考文献：
  名称：

  Asymmetric synthesis of the benzoquinoid ansamycin antitumor antibiotics: total synthesis of (+)-macbecin

  摘要：

  A convergent asymmetric synthesis of the antitumor antibiotic macbecin I has been achieved. Six of the seven stereogenic centers within the target structure were controlled using asymmetric aldol methodology, while the final stereogenic center was established through internal asymmetric induction. Fragment coupling was accomplished using a mild, titanium tetrachloride mediated aldol reaction. The C1-C5 unsaturated dienic ester was stereoselectively incorporated through a kinetically controlled Horner-Emmons olefination. Macrolactamization and subsequent refunctionalization afforded macbecin I.

  DOI：

  10.1021/jo00054a035

文献信息

• BAKER, RAYMOND;CASTRO, JOSE L., J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 47-65
  作者：BAKER, RAYMOND、CASTRO, JOSE L.

  DOI：——

  日期：——
• Asymmetric synthesis of the benzoquinoid ansamycin antitumor antibiotics: total synthesis of (+)-macbecin
  作者：David A. Evans、Scott J. Miller、Michael D. Ennis

  DOI：10.1021/jo00054a035

  日期：1993.1

  A convergent asymmetric synthesis of the antitumor antibiotic macbecin I has been achieved. Six of the seven stereogenic centers within the target structure were controlled using asymmetric aldol methodology, while the final stereogenic center was established through internal asymmetric induction. Fragment coupling was accomplished using a mild, titanium tetrachloride mediated aldol reaction. The C1-C5 unsaturated dienic ester was stereoselectively incorporated through a kinetically controlled Horner-Emmons olefination. Macrolactamization and subsequent refunctionalization afforded macbecin I.