<4R,(1'S)>-4-<2,2-bis(ethoxy)-1-hydroxy-1-ethyl>-1,3-oxathiolane-2-thione | 205525-58-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧硫杂环戊烷
• 英文名称: <4R,(1'S)>-4-<2,2-bis(ethoxy)-1-hydroxy-1-ethyl>-1,3-oxathiolane-2-thione
• CAS: 205525-58-2
• 化学式: C₉H₁₆O₄S₂
• 分子量: 252.356
• InChiKey: KQZXNOACQDISRZ-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.16
• 重原子数：
  15.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  <4R,(1'S)>-4-<2,2-bis(ethoxy)-1-hydroxy-1-ethyl>-1,3-oxathiolane-2-thione 在 2,6-二甲基吡啶 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2S,3S)-4,4-bis(ethoxy)-3-(tert-butyldimethylsilyl)oxy-1,2-epithiobutane
  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：

  γ-hydroxycrotylaldehyde diethylacetal 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 D-(-)-酒石酸二乙酯 、 sodium hydride 、 酒石酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 paraffin 为溶剂， 反应 25.33h， 生成 <4R,(1'S)>-4-<2,2-bis(ethoxy)-1-hydroxy-1-ethyl>-1,3-oxathiolane-2-thione
  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.