(+/-) 2'-(1-acetoxymethylethyl)-4-ethoxycarbonyl-2,4'-bithiazole | 160060-11-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (+/-) 2'-(1-acetoxymethylethyl)-4-ethoxycarbonyl-2,4'-bithiazole
• 英文别名: Ethyl 2-[2-(1-acetyloxypropan-2-yl)-1,3-thiazol-4-yl]-1,3-thiazole-4-carboxylate
• CAS: 160060-11-7
• 化学式: C₁₄H₁₆N₂O₄S₂
• 分子量: 340.424
• InChiKey: UVNMXZHWNKQMAR-UHFFFAOYSA-N

物化性质

• 沸点：
  475.0±53.0 °C(predicted)
• 密度：
  1.303±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (+/-) 2'-(1-acetoxymethylethyl)-4-ethoxycarbonyl-2,4'-bithiazole 在 lipase Godo E-1 作用下， 以 异丙醚 、 水 为溶剂， 反应 24.0h， 以37%的产率得到(S)-4-ethoxycarbonyl-2'-(1-hydroxymethylethyl)-2,4'-bithiazole
  参考文献：
  名称：

  Total synthesis of (4R,5S,6E,14S)- and (4R,5S,6E,14R)-cystothiazoles F

  摘要：

  Total synthesis of (4R,5S,6E,14S)- and (4R,5S,6E,14R)-cystothiazoles F 3 was achieved from the chiral bithiazole-type primary alcohols [(S)- and (R)-4-ethoxycarbonyl-2'-(1-hydroxymethylethyl)-2,4'-bithiazoles 8], which were obtained based on the enzymatic resolution of racemic alcohol 8 and its acetate 9. From a direct comparison by means of chiral HPLC between natural cystothiazole F 3 and synthetic compounds [(4R,5S,6E,14S)- and (4R,5S,6E,14R)-cystothiazoles 3], natural cystothiazole F 3 was found to be a 33:67 diastereomeric mixture [(4R,5S,6E,14S)-3:(4R,5S,6E,14R)-3 = 33:67]. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.02.011
• 作为产物：
  描述：

  在 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 15.25h， 生成 (+/-) 2'-(1-acetoxymethylethyl)-4-ethoxycarbonyl-2,4'-bithiazole
  参考文献：
  名称：

  Total synthesis of (4R,5S,6E,14S)- and (4R,5S,6E,14R)-cystothiazoles F

  摘要：

  Total synthesis of (4R,5S,6E,14S)- and (4R,5S,6E,14R)-cystothiazoles F 3 was achieved from the chiral bithiazole-type primary alcohols [(S)- and (R)-4-ethoxycarbonyl-2'-(1-hydroxymethylethyl)-2,4'-bithiazoles 8], which were obtained based on the enzymatic resolution of racemic alcohol 8 and its acetate 9. From a direct comparison by means of chiral HPLC between natural cystothiazole F 3 and synthetic compounds [(4R,5S,6E,14S)- and (4R,5S,6E,14R)-cystothiazoles 3], natural cystothiazole F 3 was found to be a 33:67 diastereomeric mixture [(4R,5S,6E,14S)-3:(4R,5S,6E,14R)-3 = 33:67]. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.02.011

文献信息

• Synthesis of Ozonolysis Products of Myxothiazol.
  作者：Hiroyuki AKITA、Masako NOZAWA、Shinji NAGUMO

  DOI：10.1248/cpb.42.1208

  日期：——

  By applying the Hantzsch thiazole procedure, the synthesis of bithiazole derivatives (2 and (±)-3) corresponding to degradation products of myxothiazol was achieved. Optically active (S)-3 (87-88% ee) and its analog (S)-16(91% ee) were obtained through enantioselective hydrolysis of the corresponding acetates ((±)-18, (±)-20 and (±)-21) using lipase in water-saturated organic solvent.

  通过应用 Hantzsch 噻唑程序，合成了与 myxothiazol 降解产物相对应的双噻唑衍生物（2 和 (±)-3）。利用脂肪酶在水饱和有机溶剂中对相应的醋酸盐（(±)-18、(±)-20 和 (±)-21）进行对映选择性水解，得到了具有光学活性的 (S)-3 (87-88% ee) 及其类似物 (S)-16 (91% ee)。