E-(3R,4R)-3-t-butyldimethylsiloxy-4-methoxy-4-methyl-1-tributylstannyl-1-octene | 134236-60-5

• 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: E-(3R,4R)-3-t-butyldimethylsiloxy-4-methoxy-4-methyl-1-tributylstannyl-1-octene
• 英文别名: tert-butyl-[(3R,4R)-4-methoxy-4-methyl-1-tributylstannyloct-1-en-3-yl]oxy-dimethylsilane
• CAS: 134236-60-5
• 化学式: C₂₈H₆₀O₂SiSn
• 分子量: 575.579
• InChiKey: YZTXLWRIBWLUBA-FNLMSBKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.92
• 重原子数：
  32
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  E-(3R,4R)-3-t-butyldimethylsiloxy-4-methoxy-4-methyl-1-tributylstannyl-1-octene 在 4-二甲氨基吡啶 、 甲基磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 (11R,12R,15R,16R)-11,15-di-t-butyldimethylsiloxy-7-hydroxy-16-methyl-16-methoxy-9-oxo-prosta-7,13-dien-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：

  三正丁基氢锡 、 (3R,4R)-3-t-butyldimethylsiloxy-4-methoxy-4-methyl-1-octyne 在 3,3'-[(E)-1,2-Diazenediyl]bis(2-methylpropanenitrile) 作用下， 以 正己烷 为溶剂， 以8.1 g (70%)的产率得到E-(3R,4R)-3-t-butyldimethylsiloxy-4-methoxy-4-methyl-1-tributylstannyl-1-octene
  参考文献：
  名称：

  Novel process and intermediates

  摘要：

  这项发明涉及制备16-甲氧基-16-甲基前列腺素E.sub.1衍生物的新工艺，以及用于该衍生物的新中间体。

  公开号：

  US05055592A1

文献信息

• A practical synthesis of the ω side-chain unit present in mexiprostil and its use for synthesis of mexiprostil via two-component coupling process.
  作者：Sentaro Okamoto、Toshiharu Yoshino、Fumie Sato

  DOI：10.1016/s0957-4166(00)82153-9

  日期：1991.1

  A practical synthesis of the optically active omega side-chain unit present in mexiprostil, a PGE1 analogue, by starting from readily available optically pure 4 has been developed. Synthesis of mexiprostil via two-component coupling process by using the omega side-chain thus prepared has been carried out.
• KOLB, MICHAEL;VAN, HIJFTE LUC
  作者：KOLB, MICHAEL、VAN, HIJFTE LUC

  DOI：——

  日期：——
• KOLB, M.;VAN, HIJFTE L.;IRELAND, R. E., TETRAHEDRON LETT., 29,(1988) N 51, C. 6769-6772
  作者：KOLB, M.、VAN, HIJFTE L.、IRELAND, R. E.

  DOI：——

  日期：——
• Novel process and intermediates
  申请人：Merrell Dow Pharmaceuticals

  公开号：US05055592A1

  公开（公告）日：1991-10-08

  This invention relates to the novel processes for the preparation of a 16-methoxy-16-methyl prostaglandin E.sub.1 derivative and to the novel intermediates useful therefor.

  这项发明涉及制备16-甲氧基-16-甲基前列腺素E.sub.1衍生物的新工艺，以及用于该衍生物的新中间体。
• Towards a large scale preparation of mexiprostil
  作者：L. Van Hijfte、M. Kolb

  DOI：10.1016/s0040-4020(01)88229-6

  日期：1992.1

  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.