(8R,11R,12R,15R,16R)-11,15-di-t-butyldimethylsiloxy-7-hydroxy-16-methyl-16-methoxy-9-oxo-prost-13-en-1-oic acid methyl ester | 125226-65-5

• 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: (8R,11R,12R,15R,16R)-11,15-di-t-butyldimethylsiloxy-7-hydroxy-16-methyl-16-methoxy-9-oxo-prost-13-en-1-oic acid methyl ester
• CAS: 125226-65-5
• 化学式: C₃₅H₆₈O₇Si₂
• 分子量: 657.092
• InChiKey: LVKYFKBUTOATEB-RVADETJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.61
• 重原子数：
  44.0
• 可旋转键数：
  18.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  91.29
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (8R,11R,12R,15R,16R)-11,15-di-t-butyldimethylsiloxy-7-hydroxy-16-methyl-16-methoxy-9-oxo-prost-13-en-1-oic acid methyl ester 在 4-二甲氨基吡啶 、 三正丁基氢锡 、 溶剂黄146 、 甲基磺酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.92h， 生成 (8R,11R,12R,15S,16S)-11,15-diydroxy-16-methyl-16-methoxy-9-oxo-prost-13-en-1-oic acid methyl ester
  参考文献：
  名称：

  Towards a large scale preparation of mexiprostil

  摘要：

  The enantioselective synthesis of mexiprostil (16R-16-methoxy-16-methyl PGE1 methyl ester) is described. The assembly of the prostaglandin framework has been accomplished by the throe component coupling process, via consecutive linking of the omega and alpha-sidechain to unsubstituted (R)-4-hydroxy-2-cyclopentenone, and alternatively by a conjugate addition of the omega-side chain to a (R)-4-hydroxy-2-cyclopentenone in which the alpha-side chain is already incorporated. The required lower side chain building block is prepared enantioselectively from nerol utilising the Sharpless expoxidation reaction.

  DOI：

  10.1016/s0040-4020(01)88229-6
• 作为产物：
  描述：

  7-氧代庚酸甲酯 、 (4R)-(+)-T-丁基二甲基硅氧-1-酮 、 E-(3R,4R)-3-t-butyldimethylsiloxy-4-methoxy-4-methyl-1-tributylstannyl-1-octene 生成 (8R,11R,12R,15R,16R)-11,15-di-t-butyldimethylsiloxy-7-hydroxy-16-methyl-16-methoxy-9-oxo-prost-13-en-1-oic acid methyl ester
  参考文献：
  名称：

  Towards a large scale preparation of mexiprostil

  摘要：

  The enantioselective synthesis of mexiprostil (16R-16-methoxy-16-methyl PGE1 methyl ester) is described. The assembly of the prostaglandin framework has been accomplished by the throe component coupling process, via consecutive linking of the omega and alpha-sidechain to unsubstituted (R)-4-hydroxy-2-cyclopentenone, and alternatively by a conjugate addition of the omega-side chain to a (R)-4-hydroxy-2-cyclopentenone in which the alpha-side chain is already incorporated. The required lower side chain building block is prepared enantioselectively from nerol utilising the Sharpless expoxidation reaction.

  DOI：

  10.1016/s0040-4020(01)88229-6