(1S,2E,4S,6S,8S,12S,14E,16S)-8-[(1S,3R)-4-[tert-butyl(dimethyl)silyl]oxy-1-(methoxymethoxy)-3-methylbutyl]-12,18,18-trimethyl-5,9,17,19-tetraoxatricyclo[14.3.0.04,6]nonadeca-2,14-dien-10-one | 1199807-73-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (1S,2E,4S,6S,8S,12S,14E,16S)-8-[(1S,3R)-4-[tert-butyl(dimethyl)silyl]oxy-1-(methoxymethoxy)-3-methylbutyl]-12,18,18-trimethyl-5,9,17,19-tetraoxatricyclo[14.3.0.04,6]nonadeca-2,14-dien-10-one
• CAS: 1199807-73-2
• 化学式: C₃₁H₅₄O₈Si
• 分子量: 582.85
• InChiKey: LXJBRGGIZUUXPE-ZDGQLRMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.16
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1S,2E,4S,6S,8S,12S,14E,16S)-8-[(1S,3R)-4-[tert-butyl(dimethyl)silyl]oxy-1-(methoxymethoxy)-3-methylbutyl]-12,18,18-trimethyl-5,9,17,19-tetraoxatricyclo[14.3.0.04,6]nonadeca-2,14-dien-10-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以89%的产率得到(1S,2E,4S,6S,8S,12S,14E,16S)-8-[(1S,3R)-4-hydroxy-1-(methoxymethoxy)-3-methylbutyl]-12,18,18-trimethyl-5,9,17,19-tetraoxatricyclo[14.3.0.04,6]nonadeca-2,14-dien-10-one
  参考文献：
  名称：

  Synthesis of the Macrocyclic Core of Iriomoteolide 3a

  摘要：

  The asymmetric synthesis of the fully functionalized macrocyclic core of iriomoteolide 3a, a cytotoxic 15-membered macrolide, Is disclosed. The key steps involve Sharpless asymmetric dihydroxylation, Sharpless asymmetric epoxidation, olefin cross-metathesis, Yamaguchi esterification, and a ring-closing metathesis reaction for macrocyclization.

  DOI：

  10.1021/ol9025183
• 作为产物：
  描述：

  [(2S,3S,5R)-6-[tert-butyl(dimethyl)silyl]oxy-1-[(2S,3S)-3-ethenyloxiran-2-yl]-3-(methoxymethoxy)-5-methylhexan-2-yl] (E,3S)-6-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylhex-5-enoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 、 (1S,2E,4S,6S,8S,12S,14E,16S)-8-[(1S,3R)-4-[tert-butyl(dimethyl)silyl]oxy-1-(methoxymethoxy)-3-methylbutyl]-12,18,18-trimethyl-5,9,17,19-tetraoxatricyclo[14.3.0.04,6]nonadeca-2,14-dien-10-one
  参考文献：
  名称：

  Synthesis of the Macrocyclic Core of Iriomoteolide 3a

  摘要：

  The asymmetric synthesis of the fully functionalized macrocyclic core of iriomoteolide 3a, a cytotoxic 15-membered macrolide, Is disclosed. The key steps involve Sharpless asymmetric dihydroxylation, Sharpless asymmetric epoxidation, olefin cross-metathesis, Yamaguchi esterification, and a ring-closing metathesis reaction for macrocyclization.

  DOI：

  10.1021/ol9025183

文献信息

• Synthesis of the Macrocyclic Core of Iriomoteolide 3a
  作者：Chada Raji Reddy、Gajula Dharmapuri、Nagavaram Narsimha Rao

  DOI：10.1021/ol9025183

  日期：2009.12.17

  The asymmetric synthesis of the fully functionalized macrocyclic core of iriomoteolide 3a, a cytotoxic 15-membered macrolide, Is disclosed. The key steps involve Sharpless asymmetric dihydroxylation, Sharpless asymmetric epoxidation, olefin cross-metathesis, Yamaguchi esterification, and a ring-closing metathesis reaction for macrocyclization.