(S)-2'-(1-tertbutyldimethylsiloxymethylethyl)-4-iodo-methyl-2,4'-bithiazole | 937184-90-2

• 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)-2'-(1-tertbutyldimethylsiloxymethylethyl)-4-iodo-methyl-2,4'-bithiazole
• CAS: 937184-90-2
• 化学式: C₁₆H₂₅IN₂OS₂Si
• 分子量: 480.509
• InChiKey: OINNDSJTPYZMQH-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.33
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  35.01
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-2'-(1-tertbutyldimethylsiloxymethylethyl)-4-iodo-methyl-2,4'-bithiazole 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 20.25h， 生成
  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：

  (+/-)-4-ethoxycarbonyl-2'-(1-hydroxymethylethyl)-2,4'-bithiazole 在 lipase Godo E-1 咪唑 、 锂硼氢 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 、 吡啶 、 异丙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.5h， 生成 (S)-2'-(1-tertbutyldimethylsiloxymethylethyl)-4-iodo-methyl-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