(S)-4-ethoxycarbonyl-2'-(1-hydroxymethylethyl)-2,4'-bithiazole | 160168-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-4-ethoxycarbonyl-2'-(1-hydroxymethylethyl)-2,4'-bithiazole
• 英文别名: ethyl 2-[2-[(2S)-1-hydroxypropan-2-yl]-1,3-thiazol-4-yl]-1,3-thiazole-4-carboxylate
• CAS: 160168-03-6
• 化学式: C₁₂H₁₄N₂O₃S₂
• 分子量: 298.387
• InChiKey: BHKHMCHLYFSVKX-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-4-ethoxycarbonyl-2'-(1-hydroxymethylethyl)-2,4'-bithiazole 在 咪唑 、 锂硼氢 、 四丁基氟化铵 、 碘 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 24.25h， 生成 (4R,5S,6E,14S)-cystothiazole F
  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：

  3-乙酰氨基硫代丙酰胺 在 重氮甲烷 、 吡啶 、 chromium(VI) oxide 、 sodium hydroxide 、 锂硼氢 、 硫酸 、 氢溴酸 、 溴 、 溶剂黄146 作用下， 以 四氢呋喃 、 异丙醚 、 水 、 丙酮 为溶剂， 反应 110.33h， 生成 (S)-4-ethoxycarbonyl-2'-(1-hydroxymethylethyl)-2,4'-bithiazole
  参考文献：
  名称：

  Synthesis of Ozonolysis Products of Myxothiazol.

  摘要：

  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)。

  DOI：

  10.1248/cpb.42.1208

文献信息

• Total synthesis of (+)-myxothiazols A and Z
  作者：Yuki Iwaki、Masahiro Kaneko、Hiroyuki Akita

  DOI：10.1016/j.tetasy.2008.12.031

  日期：2009.2

  The first synthesis of (+)-myxothiazol A 1 was achieved based on a modified Julia olefination between (3,5R)-dimethoxy-(4R)-methyl-6-oxo-(2E)-hexenamide 3, corresponding to the left side of the final molecule, and 4-(2 ''-benzothiazolyl)sulfonylmethyl-2'-[(1'''R),6"'-dimethylhepta-(2"'E),(4"'E)-dienyl]-2,4'-bithiazole 6, corresponding to the right side. The synthesis of (+)-myxothiazol Z 2 was also achieved based on modified Julia olefination between (3,5R)-dimethoxy-(4R)-methyl-6-oxo-(2E)-hexenoate 4, corresponding to left side of the final molecule, and (S)-sulfone 6. (C) 2009 Elsevier Ltd. All rights reserved.
• First synthesis of (+)-myxothiazol A
  作者：Yuki Iwaki、Masahiro Kaneko、Hiroyuki Akita

  DOI：10.1016/j.tetlet.2008.09.125

  日期：2008.12

  First convergent synthesis of (+)-myxothiazol A(1) was achieved based on modified (one-pot) Julia Olefination between (3,5R)-dimethoxy-(4R)-methyl 6-oxo-(2E)-hexenamide (2), corresponding to left-side of the final molecule, and E-4-2'-(1S,6-dimethylheptadiene)-(2,4'-bis-thiazole)-4-methybenzothiazole sulfone (4) corresponding to right-side. (C) 2008 Elsevier Ltd. All rights reserved.
• 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)。
• Total synthesis of (4R,5S,6E,14S)- and (4R,5S,6E,14R)-cystothiazoles F
  作者：Hiroyuki Akita、Yuki Iwaki、Keisuke Kato、Jianhua Qi、Makoto Ojika

  DOI：10.1016/j.tetasy.2007.02.011

  日期：2007.3

  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.