(2S,3E)-2-hydroxy-3-methyl-4-(2-methylthiazol-4-yl)but-3-enyl 4-methylphenylsulfonate | 1263941-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3E)-2-hydroxy-3-methyl-4-(2-methylthiazol-4-yl)but-3-enyl 4-methylphenylsulfonate
• 英文别名: [(E,2S)-2-hydroxy-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)but-3-enyl] 4-methylbenzenesulfonate
• CAS: 1263941-34-9
• 化学式: C₁₆H₁₉NO₄S₂
• 分子量: 353.463
• InChiKey: CRNOQOHAOBHXCP-OQRGYWNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3E)-2-hydroxy-3-methyl-4-(2-methylthiazol-4-yl)but-3-enyl 4-methylphenylsulfonate 在 吡啶 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 22.0h， 生成 (2R,3E)-3-methyl-4-(2-methylthiazol-4-yl)-1-cyanobut-3-en-2-yl 2-methoxy-2-phenyl-3,3,3-trifluoropropionate
  参考文献：
  名称：

  Synthesis of epothilones molecule fragment (15R)-C 13 -C 21 from D-mannitol

  摘要：

  Efficient synthesis of an epothilone molecules fragment (15R)-C-13-C-21 was carried out from D-mannitol through its conversion into methyl 2,3-O-cyclohexylidene-D-glycerate followed by the cyclopropanation of the ester group with ethylmagnesium bromide in the presence of titanium(IV) isopropoxide and the transformation of the obtained cyclopropanol into the corresponding 2-substituted allyl bromide. The coupling of the latter catalyzed by copper with 2-methylthiazolyl-4-magnesium bromide, the shift of a double carbon-carbon bond in the product obtained into the position, conjugated with the thiazole ring, and the common transformation of the protected 1,2-diol function afforded the target compound in 15% yield.

  DOI：

  10.1134/s1070428010110175
• 作为产物：
  描述：

  4-[(1E)-2-{(2S)-1,4-dioxaspiro[4.5]dec-2-yl}prop-1-enyl]-2-methylthiazole 在 吡啶 、 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 (2S,3E)-2-hydroxy-3-methyl-4-(2-methylthiazol-4-yl)but-3-enyl 4-methylphenylsulfonate
  参考文献：
  名称：

  Synthesis of epothilones molecule fragment (15R)-C 13 -C 21 from D-mannitol

  摘要：

  Efficient synthesis of an epothilone molecules fragment (15R)-C-13-C-21 was carried out from D-mannitol through its conversion into methyl 2,3-O-cyclohexylidene-D-glycerate followed by the cyclopropanation of the ester group with ethylmagnesium bromide in the presence of titanium(IV) isopropoxide and the transformation of the obtained cyclopropanol into the corresponding 2-substituted allyl bromide. The coupling of the latter catalyzed by copper with 2-methylthiazolyl-4-magnesium bromide, the shift of a double carbon-carbon bond in the product obtained into the position, conjugated with the thiazole ring, and the common transformation of the protected 1,2-diol function afforded the target compound in 15% yield.

  DOI：

  10.1134/s1070428010110175

文献信息

• Synthesis of epothilones molecule fragment (15R)-C 13 -C 21 from D-mannitol
  作者：V. N. Kovalenko、N. A. Sokolov、O. G. Kulinkovich

  DOI：10.1134/s1070428010110175

  日期：2010.11

  Efficient synthesis of an epothilone molecules fragment (15R)-C-13-C-21 was carried out from D-mannitol through its conversion into methyl 2,3-O-cyclohexylidene-D-glycerate followed by the cyclopropanation of the ester group with ethylmagnesium bromide in the presence of titanium(IV) isopropoxide and the transformation of the obtained cyclopropanol into the corresponding 2-substituted allyl bromide. The coupling of the latter catalyzed by copper with 2-methylthiazolyl-4-magnesium bromide, the shift of a double carbon-carbon bond in the product obtained into the position, conjugated with the thiazole ring, and the common transformation of the protected 1,2-diol function afforded the target compound in 15% yield.