methyl (2R,3S,4R,7S,8Z,10S,11S,12S,13Z,16R,17R,18R,19S,20S,21Z)-3,11,17-tris[[tert-butyl(dimethyl)silyl]oxy]-16-[[tert-butyl(dimethyl)silyl]oxymethyl]-19-carbamoyloxy-7-hydroxy-2,4,10,12,14,18,20-heptamethyl-5-oxotetracosa-8,13,21,23-tetraenoate | 646031-64-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl (2R,3S,4R,7S,8Z,10S,11S,12S,13Z,16R,17R,18R,19S,20S,21Z)-3,11,17-tris[[tert-butyl(dimethyl)silyl]oxy]-16-[[tert-butyl(dimethyl)silyl]oxymethyl]-19-carbamoyloxy-7-hydroxy-2,4,10,12,14,18,20-heptamethyl-5-oxotetracosa-8,13,21,23-tetraenoate
• CAS: 646031-64-3
• 化学式: C₅₈H₁₁₃NO₁₀Si₄
• 分子量: 1096.88
• InChiKey: PFEHNTRNQYXSQM-JJNFTLJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.2
• 重原子数：
  73
• 可旋转键数：
  35
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  153
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl (2R,3S,4R,7S,8Z,10S,11S,12S,13Z,16R,17R,18R,19S,20S,21Z)-3,11,17-tris[[tert-butyl(dimethyl)silyl]oxy]-16-[[tert-butyl(dimethyl)silyl]oxymethyl]-19-carbamoyloxy-7-hydroxy-2,4,10,12,14,18,20-heptamethyl-5-oxotetracosa-8,13,21,23-tetraenoate 在 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以73%的产率得到
  参考文献：
  名称：

  Synthesis of novel discodermolide analogues with modified hydrogen-bonding donor/acceptor sites

  摘要：

  A series of novel structural analogues of the potent microtubule-stabilizing anticancer agent discodermolide were synthesised, with modifications in the C16-C20 region to create new oxygenated H-bonding donor/acceptor sites for tubulin binding. By starting from an advanced C9-C24 intermediate, fully synthetic discodermolide analogues, incorporating either an additional hydroxyl group 3, an oxetane 4 or a cyclic carbonate 5, were obtained in 10 or 11 steps by using a versatile aldol construction of the C6-C7 bond. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.172
• 作为产物：
  描述：

  (2Z,7Z,15Z)-(4S,5S,6S,10R,11R,12R,13S,14S)-5,11-Bis-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-dimethyl-silanyloxymethyl)-13-hydroxy-4,6,8,12,14-pentamethyl-octadeca-2,7,15,17-tetraenoic acid methyl ester 在 (+)-β-chlorodiisopinocampheylborane 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 methyl (2R,3S,4R,7S,8Z,10S,11S,12S,13Z,16R,17R,18R,19S,20S,21Z)-3,11,17-tris[[tert-butyl(dimethyl)silyl]oxy]-16-[[tert-butyl(dimethyl)silyl]oxymethyl]-19-carbamoyloxy-7-hydroxy-2,4,10,12,14,18,20-heptamethyl-5-oxotetracosa-8,13,21,23-tetraenoate
  参考文献：
  名称：

  Synthesis of novel discodermolide analogues with modified hydrogen-bonding donor/acceptor sites

  摘要：

  A series of novel structural analogues of the potent microtubule-stabilizing anticancer agent discodermolide were synthesised, with modifications in the C16-C20 region to create new oxygenated H-bonding donor/acceptor sites for tubulin binding. By starting from an advanced C9-C24 intermediate, fully synthetic discodermolide analogues, incorporating either an additional hydroxyl group 3, an oxetane 4 or a cyclic carbonate 5, were obtained in 10 or 11 steps by using a versatile aldol construction of the C6-C7 bond. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.172

文献信息

• Synthesis of novel discodermolide analogues with modified hydrogen-bonding donor/acceptor sites
  作者：Ian Paterson、Oscar Delgado

  DOI：10.1016/j.tetlet.2003.09.172

  日期：2003.12

  A series of novel structural analogues of the potent microtubule-stabilizing anticancer agent discodermolide were synthesised, with modifications in the C16-C20 region to create new oxygenated H-bonding donor/acceptor sites for tubulin binding. By starting from an advanced C9-C24 intermediate, fully synthetic discodermolide analogues, incorporating either an additional hydroxyl group 3, an oxetane 4 or a cyclic carbonate 5, were obtained in 10 or 11 steps by using a versatile aldol construction of the C6-C7 bond. (C) 2003 Elsevier Ltd. All rights reserved.