S-tert-Butyl (2R^*,3R^*)-2-butyl-3-hydroxy-4-pentynethioate

• 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: S-tert-Butyl (2R^*,3R^*)-2-butyl-3-hydroxy-4-pentynethioate
• 英文别名: S-tert-butyl (2R)-2-[(1R)-1-hydroxyprop-2-ynyl]hexanethioate
• 化学式: C₁₃H₂₂O₂S
• 分子量: 242.382
• InChiKey: XTVJUNWQMIBPEN-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-tert-Butyl (2R^*,3R^*)-2-butyl-3-hydroxy-4-pentynethioate 在 Lindlar's catalyst 氢气 作用下， 以 乙醇 为溶剂， 60.0 ℃ 、101.32 kPa 条件下， 反应 1.0h， 以85%的产率得到S-tert-Butyl (2R^*,3R^*)-2-butyl-3-hydroxy-4-pentenethioate
  参考文献：
  名称：

  High diastereoselective aldol reactions of cobalt-complexed and uncomplexed propynals with an O-silyl ketene O,S-acetal: highly stereoselective total syntheses of (.+-.)-blastmycinone and its three diastereoisomers from 3-(trimethylsilyl)propynal

  摘要：

  Total syntheses of (+/-)-blastmycinone (2) and its three diastereoisomers (3-5) are described. The syntheses involve highly stereoselective aldol reactions of cobalt-complexed propynal 6 and uncomplexed propynal 7 with O-silyl ketene O,S-acetal 8, which possesses an n-butyl tether, under Mukaiyama conditions. (+/-)-Blastmycinone (2) and its 2-epimer 3 were stereoselectively synthesized through chelation-controlled reduction, whereas (+/-)-3-epi- and 4-epiblastmycinone (5 and 4) were obtained in a highly stereocontrolled manner with bromolactonization as a key step.

  DOI：

  10.1021/jo00063a008
• 作为产物：
  描述：

  S-tert-Butyl (2R^*,3R^*)-2-butyl-3-hydroxy-5-(trimethylsilyl)-4-pentynethioate 在 氢氟酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以82%的产率得到S-tert-Butyl (2R^*,3R^*)-2-butyl-3-hydroxy-4-pentynethioate
  参考文献：
  名称：

  High diastereoselective aldol reactions of cobalt-complexed and uncomplexed propynals with an O-silyl ketene O,S-acetal: highly stereoselective total syntheses of (.+-.)-blastmycinone and its three diastereoisomers from 3-(trimethylsilyl)propynal

  摘要：

  Total syntheses of (+/-)-blastmycinone (2) and its three diastereoisomers (3-5) are described. The syntheses involve highly stereoselective aldol reactions of cobalt-complexed propynal 6 and uncomplexed propynal 7 with O-silyl ketene O,S-acetal 8, which possesses an n-butyl tether, under Mukaiyama conditions. (+/-)-Blastmycinone (2) and its 2-epimer 3 were stereoselectively synthesized through chelation-controlled reduction, whereas (+/-)-3-epi- and 4-epiblastmycinone (5 and 4) were obtained in a highly stereocontrolled manner with bromolactonization as a key step.

  DOI：

  10.1021/jo00063a008

文献信息

• High diastereoselective aldol reactions of cobalt-complexed and uncomplexed propynals with an O-silyl ketene O,S-acetal: highly stereoselective total syntheses of (.+-.)-blastmycinone and its three diastereoisomers from 3-(trimethylsilyl)propynal
  作者：Chisato Mukai、Osamu Kataoka、Miyoji Hanaoka

  DOI：10.1021/jo00063a008

  日期：1993.5

  Total syntheses of (+/-)-blastmycinone (2) and its three diastereoisomers (3-5) are described. The syntheses involve highly stereoselective aldol reactions of cobalt-complexed propynal 6 and uncomplexed propynal 7 with O-silyl ketene O,S-acetal 8, which possesses an n-butyl tether, under Mukaiyama conditions. (+/-)-Blastmycinone (2) and its 2-epimer 3 were stereoselectively synthesized through chelation-controlled reduction, whereas (+/-)-3-epi- and 4-epiblastmycinone (5 and 4) were obtained in a highly stereocontrolled manner with bromolactonization as a key step.