2,2-Dimethyl-propionic acid (E)-(4R,5S)-5-(tert-butyl-dimethyl-silanyloxy)-5-{(2R,3R)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-oxiranyl}-2,4-dimethyl-pent-2-enyl ester | 882491-55-6

• 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: 2,2-Dimethyl-propionic acid (E)-(4R,5S)-5-(tert-butyl-dimethyl-silanyloxy)-5-{(2R,3R)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-oxiranyl}-2,4-dimethyl-pent-2-enyl ester
• 英文别名: [(E,4R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-5-[(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxybut-3-enyl]oxiran-2-yl]-2,4-dimethylpent-2-enyl] 2,2-dimethylpropanoate
• CAS: 882491-55-6
• 化学式: C₃₀H₅₈O₅Si₂
• 分子量: 554.959
• InChiKey: YLJBAXBQJILXBW-TYKDQTPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.28
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Acetic acid (S)-1-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-but-3-enyl ester 、 2,2-Dimethyl-propionic acid (E)-(4R,5S)-5-(tert-butyl-dimethyl-silanyloxy)-5-{(2R,3R)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-oxiranyl}-2,4-dimethyl-pent-2-enyl ester 在 ruthenium carbene complex 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以68%的产率得到2,2-Dimethyl-propionic acid (E)-(4R,5S)-5-{(2R,3R)-3-[(E)-(1R,6S,7S)-6-acetoxy-1,9-bis-(tert-butyl-dimethyl-silanyloxy)-7-methyl-non-3-enyl]-oxiranyl}-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pent-2-enyl ester
  参考文献：
  名称：

  Enantioselective Total Synthesis of FD-891

  摘要：

  The enantioselective synthesis of FD-891 has been achieved with a longest linear sequence of 21 steps. The synthetic strategy involves the use of aldol additions of a chlorotitanium enolate of N-acylthiazolidinethiones as the key reaction to establish 6 of the 10 stereogenic centers. A key cross-metathesis and a late-stage Julia olefination serve to assemble three key subunits.

  DOI：

  10.1021/ja060018v
• 作为产物：
  描述：

  2,2-Dimethyl-propionic acid (2E,6E)-(4R,5R)-5,8-bis-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-octa-2,6-dienyl ester 在 titanium(IV) isopropylate 、 氟化铵 、 L-(+)-酒石酸二乙酯 、 4 A molecular sieve 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 magnesium bromide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 70.67h， 生成 2,2-Dimethyl-propionic acid (E)-(4R,5S)-5-(tert-butyl-dimethyl-silanyloxy)-5-{(2R,3R)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-oxiranyl}-2,4-dimethyl-pent-2-enyl ester
  参考文献：
  名称：

  Enantioselective Total Synthesis of FD-891

  摘要：

  The enantioselective synthesis of FD-891 has been achieved with a longest linear sequence of 21 steps. The synthetic strategy involves the use of aldol additions of a chlorotitanium enolate of N-acylthiazolidinethiones as the key reaction to establish 6 of the 10 stereogenic centers. A key cross-metathesis and a late-stage Julia olefination serve to assemble three key subunits.

  DOI：

  10.1021/ja060018v

文献信息

• Enantioselective Total Synthesis of FD-891
  作者：Michael T. Crimmins、Franck Caussanel

  DOI：10.1021/ja060018v

  日期：2006.3.1

  The enantioselective synthesis of FD-891 has been achieved with a longest linear sequence of 21 steps. The synthetic strategy involves the use of aldol additions of a chlorotitanium enolate of N-acylthiazolidinethiones as the key reaction to establish 6 of the 10 stereogenic centers. A key cross-metathesis and a late-stage Julia olefination serve to assemble three key subunits.