(E)-(4R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(2-methoxy-ethoxymethoxy)-hex-2-enoic acid (R)-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl ester | 913563-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-(4R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(2-methoxy-ethoxymethoxy)-hex-2-enoic acid (R)-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl ester
• CAS: 913563-38-9
• 化学式: C₂₇H₄₅NO₆SSi
• 分子量: 539.809
• InChiKey: IOPCTFLLKLBJBV-QRUGVCRUSA-N

物化性质

• 沸点：
  564.5±50.0 °C(predicted)
• 密度：
  1.050±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.31
• 重原子数：
  36.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  76.11
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (E)-(4R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(2-methoxy-ethoxymethoxy)-hex-2-enoic acid (R)-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 4-二甲氨基吡啶 、 四丁基氟化铵 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 87.0h， 生成 (4S,7E,10R,13E,15R,16S)-15-hydroxy-4,16-dimethyl-10-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,12-trione
  参考文献：
  名称：

  Synthesis of Macrosphelides with a Thiazole Side Chain:  New Antitumor Candidates Having Apoptosis-Inducing Property

  摘要：

  Hybrid compounds of macrosphelides and epothilones, both of which are natural macrolides having a 16-membered skeleton, were designed and synthesized using a ring-closing metathesis (RCM) strategy. Some of these hybrids were found to exhibit notable apoptosis-inducing activity against human lymphoma cells with higher potency than parent natural macrosphelides, and to be a promising lead compound for development of a new antitumor agent.

  DOI：

  10.1021/ol061922v
• 作为产物：
  描述：

  (1E)(3R)-2-methyl-1-[2-methyl(1,3-thiazol-4-yl)]hexa-1,5-dien-3-ol 、 (4R,5S)-5-(tert-butyldimethylsilyloxy)-4-[(2-methoxyethoxy)methoxy]-2-hexenoic acid 在 2,4,6-三氯苯甲酰氯 、 三乙胺 、 4-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以80%的产率得到(E)-(4R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(2-methoxy-ethoxymethoxy)-hex-2-enoic acid (R)-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl ester
  参考文献：
  名称：

  Synthesis of Macrosphelides with a Thiazole Side Chain:  New Antitumor Candidates Having Apoptosis-Inducing Property

  摘要：

  Hybrid compounds of macrosphelides and epothilones, both of which are natural macrolides having a 16-membered skeleton, were designed and synthesized using a ring-closing metathesis (RCM) strategy. Some of these hybrids were found to exhibit notable apoptosis-inducing activity against human lymphoma cells with higher potency than parent natural macrosphelides, and to be a promising lead compound for development of a new antitumor agent.

  DOI：

  10.1021/ol061922v