(2R,3S)-1-[(4S)-4-benzyl-2-sulfanylidene-1,3-thiazolidin-3-yl]-2-methyl-3-triethylsilyloxyhex-5-en-1-one | 882491-63-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (2R,3S)-1-[(4S)-4-benzyl-2-sulfanylidene-1,3-thiazolidin-3-yl]-2-methyl-3-triethylsilyloxyhex-5-en-1-one
• CAS: 882491-63-6
• 化学式: C₂₃H₃₅NO₂S₂Si
• 分子量: 449.754
• InChiKey: AYHCUKJOYJLFEV-GIVPXCGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.06
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  86.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-1-[(4S)-4-benzyl-2-sulfanylidene-1,3-thiazolidin-3-yl]-2-methyl-3-triethylsilyloxyhex-5-en-1-one 在 锂硼氢 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 18.33h， 生成 (3S,4S)-3-Methyl-4-triethylsilanyloxy-hept-6-enenitrile
  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：

  1-[(4R)-4-(苯基甲基)-2-硫代-3-噻唑烷基]-1-丙酮 在 2,6-二甲基吡啶 、 四氯化钛 、 鹰爪豆碱 作用下， 以 二氯甲烷 为溶剂， 反应 1.83h， 生成 (2R,3S)-1-[(4S)-4-benzyl-2-sulfanylidene-1,3-thiazolidin-3-yl]-2-methyl-3-triethylsilyloxyhex-5-en-1-one
  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.