(Z)-(4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-6-methoxy-2,4-dimethyl-hept-2-enoic acid ethyl ester | 944823-24-9

• 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: (Z)-(4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-6-methoxy-2,4-dimethyl-hept-2-enoic acid ethyl ester
• 英文别名: ethyl (Z,4R,5S,6S)-5-[tert-butyl(dimethyl)silyl]oxy-7-[tert-butyl(diphenyl)silyl]oxy-6-methoxy-2,4-dimethylhept-2-enoate
• CAS: 944823-24-9
• 化学式: C₃₄H₅₄O₅Si₂
• 分子量: 598.971
• InChiKey: NMNIPXDBCAYTKY-KMWTXQKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.11
• 重原子数：
  41
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-(4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-6-methoxy-2,4-dimethyl-hept-2-enoic acid ethyl ester 在 咪唑 、 manganese(IV) oxide 、 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 (5R,8R,9S,10S,Z)-5-((R)-but-3-en-2-yl)-9-((tert-butyldimethylsilyl)oxy)-3,3-diethyl-10-methoxy-6,8,14,14-tetramethyl-13,13-diphenyl-4,12-dioxa-3,13-disilapentadec-6-ene
  参考文献：
  名称：

  Synthesis of migrastatin and its macrolide core

  摘要：

  Migrastatin and its macrolactone subunit are potent antimetastatic agents. Both were synthesized by using a ring-closing metathesis (RCM) to establish the macrolactone core, and the control of the (Z)-trisubstituted double bond at C11-C12 was achieved by using a Still-Gennari olefination. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.107
• 作为产物：
  描述：

  (2S,3S,4R)-3-(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenyl-silyloxy)-2-methoxy-4-methyl-hex-5-ene 在 sodium periodate 、 四氧化锇 、 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 28.0h， 生成 (Z)-(4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-6-methoxy-2,4-dimethyl-hept-2-enoic acid ethyl ester
  参考文献：
  名称：

  Synthesis of migrastatin and its macrolide core

  摘要：

  Migrastatin and its macrolactone subunit are potent antimetastatic agents. Both were synthesized by using a ring-closing metathesis (RCM) to establish the macrolactone core, and the control of the (Z)-trisubstituted double bond at C11-C12 was achieved by using a Still-Gennari olefination. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.107

文献信息

• Synthesis of migrastatin and its macrolide core
  作者：Sébastien Reymond、Janine Cossy

  DOI：10.1016/j.tet.2007.02.107

  日期：2007.6

  Migrastatin and its macrolactone subunit are potent antimetastatic agents. Both were synthesized by using a ring-closing metathesis (RCM) to establish the macrolactone core, and the control of the (Z)-trisubstituted double bond at C11-C12 was achieved by using a Still-Gennari olefination. (C) 2007 Elsevier Ltd. All rights reserved.