4,4,4-tris(methylthio)-2,2-dimethyl-1,3-butanediol | 223710-63-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4,4-tris(methylthio)-2,2-dimethyl-1,3-butanediol
• 英文别名: 2,2-Dimethyl-4,4,4-tris(methylsulfanyl)butane-1,3-diol
• CAS: 223710-63-2
• 化学式: C₉H₂₀O₂S₃
• 分子量: 256.455
• InChiKey: VVLAQPLGRPEYCP-UHFFFAOYSA-N

物化性质

• 沸点：
  423.3±45.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,4,4-tris(methylthio)-2,2-dimethyl-1,3-butanediol 在 吡啶 、 tetrafluoroboric acid 、 pyrophosphatase 、 pyruvate kinase 、 Crotalus atrox venom nucleotide pyrophosphatase EC 3.6.1.9 、 dephosphocoenzyme A kinase 、 phospho(enol) pyruvate 、 phosphopantetheine adenylyltransferase 、 potato acid phosphatase EC 3.1.3.2 、 cesium fluoride 、 magnesium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 243.0h， 生成 D-(-)-泛酰内酯
  参考文献：
  名称：

  Development of a Second Generation Coenzyme A Analogue Synthon

  摘要：

  We have previously reported a general synthetic approach to analogues of coenzyme A (CoA) which involves enzymatic synthesis of a general CoA analogue synthon having a thioester linkage in place of the amide bond nearest the thiol group (Martin et al. J. Am. Chem. Sec. 1994, 116, 4660), We report here the synthesis of a second CoA analogue synthon 1c which has the amide bond more distant from the thiol group replaced with a thioester, This analogue was prepared by nonenzymatic synthesis of a racemic phosphopantetheine analogue followed by enzymatic conversion to the corresponding CoA analogue. Stereochemical analysis showed that the natural enantiomer of the phosphopantetheine analogue was selectively converted to product by the enzyme phosphopantetheine adenylyltansferase, yielding a product that possessed the desired stereoconfiguration. Reaction of the new synthon 1c with a primary amine results in amide bond formation to form the CoA analogue of interest. This new methodology provides access to an even broader array of CoA analogues modified in the beta-alanylcysteamine moiety, This has been demonstrated in the synthesis of an analogue having an extra methylene group in the beta-alanine moiety and two analogues in which the amide bond nearest the thiol group is replaced with a pair of methylene groups.

  DOI：

  10.1021/jo981758s
• 作为产物：
  描述：

  2,2-二甲基-3-羟基丙醛 、 三(甲基硫代)甲烷 在 正丁基锂 作用下， 生成 4,4,4-tris(methylthio)-2,2-dimethyl-1,3-butanediol
  参考文献：
  名称：

  Development of a Second Generation Coenzyme A Analogue Synthon

  摘要：

  We have previously reported a general synthetic approach to analogues of coenzyme A (CoA) which involves enzymatic synthesis of a general CoA analogue synthon having a thioester linkage in place of the amide bond nearest the thiol group (Martin et al. J. Am. Chem. Sec. 1994, 116, 4660), We report here the synthesis of a second CoA analogue synthon 1c which has the amide bond more distant from the thiol group replaced with a thioester, This analogue was prepared by nonenzymatic synthesis of a racemic phosphopantetheine analogue followed by enzymatic conversion to the corresponding CoA analogue. Stereochemical analysis showed that the natural enantiomer of the phosphopantetheine analogue was selectively converted to product by the enzyme phosphopantetheine adenylyltansferase, yielding a product that possessed the desired stereoconfiguration. Reaction of the new synthon 1c with a primary amine results in amide bond formation to form the CoA analogue of interest. This new methodology provides access to an even broader array of CoA analogues modified in the beta-alanylcysteamine moiety, This has been demonstrated in the synthesis of an analogue having an extra methylene group in the beta-alanine moiety and two analogues in which the amide bond nearest the thiol group is replaced with a pair of methylene groups.

  DOI：

  10.1021/jo981758s