(2R,3S)-4,4-bis(ethoxy)-1,3-di(tert-butyldimethylsilyl)oxybutane-2-thiol | 205525-63-9

• 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: (2R,3S)-4,4-bis(ethoxy)-1,3-di(tert-butyldimethylsilyl)oxybutane-2-thiol
• 英文别名: (2R,3S)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]-4,4-diethoxybutane-2-thiol
• CAS: 205525-63-9
• 化学式: C₂₀H₄₆O₄SSi₂
• 分子量: 438.82
• InChiKey: OTEKFRFKMGEWFZ-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S)-4,4-bis(ethoxy)-1,3-di(tert-butyldimethylsilyl)oxybutane-2-thiol 在 camphor-10-sulfonic acid 作用下， 以 苯 为溶剂， 反应 1.0h， 以48%的产率得到(2R,3R,4R)-2-ethoxy-3-(tert-butyldimethylsilyl)oxy-4-(tert-butyldimethylsilyl)oxymethylthietane
  参考文献：
  名称：

  Asymmetric Synthesis of Thietanose

  摘要：

  Syntheses of optically active thietanose, (2R,3R,4R)-4-acetoxymethyl-3-(tert-butyldimethylsilyl)oxy-2-ethoxythietane (6) and (2R,3R,4R)-3-(tertbutyldimethylsilyl)oxy-4-[(tert-butyldimethylsilyl)oxy]methyl-2-ethoxythietane (23) are described. The key intermediate, (2S,3S)-4,4-bis(ethoxy)-3-(tertbutyldimethylsilyl)oxy-1,2-epithiobutane (7) has been derived from (Z)-2-butene-1,4-diol in 13 steps. Although direct transformation of 7 to thietanose (6) failed, regio and stereospecific ring opening of the episulfide ring in 7 and acid catalyzed cyclization of the resulting 3-mercaptobutanal diethyl acetal (20) was successful in forming of a thietane ring to give 6. The structure of 6 and 23 was confirmed by spectroscopic analyses including NOE experiments.

  DOI：

  10.3987/com-97-s(n)67
• 作为产物：
  描述：

  (2S,3S)-4,4-bis(ethoxy)-3-(tert-butyldimethylsilyl)oxy-1,2-epithiobutane 在 2,6-二甲基吡啶 、 三苯基氯甲烷 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.75h， 生成 (2R,3S)-4,4-bis(ethoxy)-1,3-di(tert-butyldimethylsilyl)oxybutane-2-thiol
  参考文献：
  名称：

  Asymmetric Synthesis of Thietanose

  摘要：

  Syntheses of optically active thietanose, (2R,3R,4R)-4-acetoxymethyl-3-(tert-butyldimethylsilyl)oxy-2-ethoxythietane (6) and (2R,3R,4R)-3-(tertbutyldimethylsilyl)oxy-4-[(tert-butyldimethylsilyl)oxy]methyl-2-ethoxythietane (23) are described. The key intermediate, (2S,3S)-4,4-bis(ethoxy)-3-(tertbutyldimethylsilyl)oxy-1,2-epithiobutane (7) has been derived from (Z)-2-butene-1,4-diol in 13 steps. Although direct transformation of 7 to thietanose (6) failed, regio and stereospecific ring opening of the episulfide ring in 7 and acid catalyzed cyclization of the resulting 3-mercaptobutanal diethyl acetal (20) was successful in forming of a thietane ring to give 6. The structure of 6 and 23 was confirmed by spectroscopic analyses including NOE experiments.

  DOI：

  10.3987/com-97-s(n)67

文献信息

• Asymmetric Synthesis of Thietanose
  作者：Jun'ichi Uenishi、Mitsuhiro Motoyama、Yumi Kimura、Osamu Yonemitsu

  DOI：10.3987/com-97-s(n)67

  日期：——

  Syntheses of optically active thietanose, (2R,3R,4R)-4-acetoxymethyl-3-(tert-butyldimethylsilyl)oxy-2-ethoxythietane (6) and (2R,3R,4R)-3-(tertbutyldimethylsilyl)oxy-4-[(tert-butyldimethylsilyl)oxy]methyl-2-ethoxythietane (23) are described. The key intermediate, (2S,3S)-4,4-bis(ethoxy)-3-(tertbutyldimethylsilyl)oxy-1,2-epithiobutane (7) has been derived from (Z)-2-butene-1,4-diol in 13 steps. Although direct transformation of 7 to thietanose (6) failed, regio and stereospecific ring opening of the episulfide ring in 7 and acid catalyzed cyclization of the resulting 3-mercaptobutanal diethyl acetal (20) was successful in forming of a thietane ring to give 6. The structure of 6 and 23 was confirmed by spectroscopic analyses including NOE experiments.