(4S,7R,8S,9S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9-tetramethyl-11-(phenylsulfonyl)undec-1-en-6-one | 308357-55-3

• 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: (4S,7R,8S,9S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9-tetramethyl-11-(phenylsulfonyl)undec-1-en-6-one
• 英文别名: (4S,7R,8S,9S)-11-(benzenesulfonyl)-4,8-bis[[tert-butyl(dimethyl)silyl]oxy]-5,5,7,9-tetramethylundec-1-en-6-one
• CAS: 308357-55-3
• 化学式: C₃₃H₆₀O₅SSi₂
• 分子量: 625.073
• InChiKey: STIKASBGJAHSEM-YJAMSFDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.07
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-{(1E,3S,5Z)-7-iodo-3-[(4-methoxybenzyl)oxy]-2,6-dimethyl-hepta-1,5-dienyl}-2-methyl-1,3-thiazole 、 (4S,7R,8S,9S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9-tetramethyl-11-(phenylsulfonyl)undec-1-en-6-one 在 正丁基锂 作用下， 生成 tert-butyl-[(2Z,5S,6E)-5-[(4-methoxyphenyl)methoxy]-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienoxy]-dimethylsilane 、 (4S,7E,9S,13Z,16S,17E)-11-(benzenesulfonyl)-4-[tert-butyl(dimethyl)silyl]oxy-16-[(4-methoxyphenyl)methoxy]-5,5,7,9,13,17-hexamethyl-18-(2-methyl-1,3-thiazol-4-yl)octadeca-1,7,13,17-tetraen-6-one
  参考文献：
  名称：

  Epothilone B and its Derivatives as Novel Antitumor Drugs: Total and Partial Synthesis and Biological Evaluation

  摘要：

  Microtubule stabilizing natural products, as exemplified by paclitaxel (taxol(R)), are being considered as novel drugs against malignant therapy resistent solid tumors. Among these compounds, epothilone B and some of its derivatives have emerged as particularly promising candidates for industrial development. The total and partial syntheses of these compounds are described in detail, and some of the most important recent results on their biological activity are discussed.

  DOI：

  10.1007/s007060070099
• 作为产物：
  描述：

  3,3-dimethyl-4-oxohex-1-ene 在 2,6-二甲基吡啶 、 臭氧 、 (-)-diisopinocamphenylborane chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 14.17h， 生成 (4S,7R,8S,9S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9-tetramethyl-11-(phenylsulfonyl)undec-1-en-6-one
  参考文献：
  名称：

  埃博霉素B和D的总合成。

  摘要：

  从光学纯的（S）-苹果酸和（R）-3-羟基-2-甲基丙酸甲酯开始，描述了微管稳定的抗肿瘤药物埃博霉素B和D的总合成。通过偶联三个片段C1-C6（片段D），C7-C10（片段C）和C11-C21（片段B），合成高度收敛。关键步骤是两个立体选择性Wittig型烯烃生成12,13-和16,17-双键，对映选择性Mukaiyama aldol加成以合成片段D，以及砜阴离子烯丙基碘烷基化以连接片段B和C。最后是片段D通过羟醛加成连接到B + C片段。

  DOI：

  10.1021/jo0007480

文献信息

• Total Syntheses of Epothilones B and D
  作者：Johann Mulzer、Andreas Mantoulidis、Elisabeth Öhler

  DOI：10.1021/jo0007480

  日期：2000.11.1

  described, starting from optically pure (S)-malic acid and methyl (R)-3-hydroxy-2-methylpropionate. The synthesis is highly convergent by coupling the three fragments C1-C6 (fragment D), C7-C10 (fragment C), and C11-C21 (fragment B). Key steps are two stereoselective Wittig type olefinations to generate the 12,13- and 16,17-double bonds, an enantioselective Mukaiyama aldol addition to synthesize fragment

  从光学纯的（S）-苹果酸和（R）-3-羟基-2-甲基丙酸甲酯开始，描述了微管稳定的抗肿瘤药物埃博霉素B和D的总合成。通过偶联三个片段C1-C6（片段D），C7-C10（片段C）和C11-C21（片段B），合成高度收敛。关键步骤是两个立体选择性Wittig型烯烃生成12,13-和16,17-双键，对映选择性Mukaiyama aldol加成以合成片段D，以及砜阴离子烯丙基碘烷基化以连接片段B和C。最后是片段D通过羟醛加成连接到B + C片段。
• Epothilone B and its Derivatives as Novel Antitumor Drugs: Total and Partial Synthesis and Biological Evaluation
  作者：Johann Mulzer

  DOI：10.1007/s007060070099

  日期：2000.3.16

  Microtubule stabilizing natural products, as exemplified by paclitaxel (taxol(R)), are being considered as novel drugs against malignant therapy resistent solid tumors. Among these compounds, epothilone B and some of its derivatives have emerged as particularly promising candidates for industrial development. The total and partial syntheses of these compounds are described in detail, and some of the most important recent results on their biological activity are discussed.