7-hydroxy-11-O-(tert-butyldimethylsilyl)-15-O-<(2-methoxyethoxy)methyl>PGE₁ methyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 7-hydroxy-11-O-(tert-butyldimethylsilyl)-15-O-<(2-methoxyethoxy)methyl>PGE₁ methyl ester
• 英文别名: methyl 7-[(1S,2R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(E)-3-(2-methoxyethoxymethoxy)oct-1-enyl]-5-oxocyclopentyl]-7-hydroxyheptanoate
• 化学式: C₃₁H₅₈O₈Si
• 分子量: 586.882
• InChiKey: TXNZEFWXAGSEPE-OAHITEERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.21
• 重原子数：
  40
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  7-氧代庚酸甲酯 、 (4R)-(+)-T-丁基二甲基硅氧-1-酮 、 1-octyn-3-ol (2-methoxyethoxy)methyl ether 在 Schwartz's reagent 、 甲基锂 、 Dimethylzinc 作用下， 生成 7-hydroxy-11-O-(tert-butyldimethylsilyl)-15-O-<(2-methoxyethoxy)methyl>PGE₁ methyl ester
  参考文献：
  名称：

  A Practical, General Three-Component Coupling Approach to Prostaglandin and Non-Prostaglandin-Related Skeleta

  摘要：

  Starting with a terminal alkyne, a one-pot, six-step sequence has been developed which results in prostaglandin and related skeleta in high. yields. The method involves a transmetalation between organozirconium and cuprate species, as well as another between a copper enolate and organozincate reagent. Only catalytic amounts of the cuprate are needed. A variety of cyclic and acyclic enones participate in these multiple couplings, demonstrating that the methodology applies to far more than just the prostaglandin nucleus.

  DOI：

  10.1021/ja00105a010

文献信息

• A Practical, General Three-Component Coupling Approach to Prostaglandin and Non-Prostaglandin-Related Skeleta
  作者：Bruce H. Lipshutz、Michael R. Wood

  DOI：10.1021/ja00105a010

  日期：1994.12

  Starting with a terminal alkyne, a one-pot, six-step sequence has been developed which results in prostaglandin and related skeleta in high. yields. The method involves a transmetalation between organozirconium and cuprate species, as well as another between a copper enolate and organozincate reagent. Only catalytic amounts of the cuprate are needed. A variety of cyclic and acyclic enones participate in these multiple couplings, demonstrating that the methodology applies to far more than just the prostaglandin nucleus.