Carbamic acid (Z)-(1S,2S)-1-((S)-1-{(2R,3R)-3-[(2Z,7Z)-(4S,5S,6S,9S)-5,9-dihydroxy-10-((2S,3R,4S,5R)-4-hydroxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-2,4,6-trimethyl-deca-2,7-dienyl]-oxetan-2-yl}-ethyl)-2-methyl-hexa-3,5-dienyl ester | 646031-59-6

• 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: Carbamic acid (Z)-(1S,2S)-1-((S)-1-{(2R,3R)-3-[(2Z,7Z)-(4S,5S,6S,9S)-5,9-dihydroxy-10-((2S,3R,4S,5R)-4-hydroxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-2,4,6-trimethyl-deca-2,7-dienyl]-oxetan-2-yl}-ethyl)-2-methyl-hexa-3,5-dienyl ester
• CAS: 646031-59-6
• 化学式: C₃₃H₅₃NO₈
• 分子量: 591.786
• InChiKey: WZFVFRJNERVHDL-LITPKTQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  42.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  148.54
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Carbamic acid (Z)-(1S,2S)-1-((S)-1-{(2R,3R)-3-[(2Z,7Z)-(4S,5S,6S,9S)-5,9-dihydroxy-10-((2S,3R,4S,5R)-4-hydroxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-2,4,6-trimethyl-deca-2,7-dienyl]-oxetan-2-yl}-ethyl)-2-methyl-hexa-3,5-dienyl ester 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 (4S,5R,6S)-4-[(3Z,8Z)-(1R,5S,6S,7S,10S)-6,10-Dihydroxy-11-((2S,3R,4S,5R)-4-hydroxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-1-hydroxymethyl-3,5,7-trimethyl-undeca-3,8-dienyl]-5-methyl-6-((Z)-(S)-1-methyl-penta-2,4-dienyl)-[1,3]dioxan-2-one
  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：

  (3Z,5S,6S,7R,8S,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-[(2,4,6-trimethylphenyl)sulfoxymethyl]-5,7,11,13,15-pentamethyl-hexadeca-1,3,11-trien-8-ol 在 盐酸 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 (+)-β-chlorodiisopinocampheylborane 、 18-冠醚-6 、 碘苯二乙酸 、 potassium tert-butylate 、 二异丁基氢化铝 、 potassium carbonate 、 戴斯-马丁氧化剂 、 溶剂黄146 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 36.0h， 生成 Carbamic acid (Z)-(1S,2S)-1-((S)-1-{(2R,3R)-3-[(2Z,7Z)-(4S,5S,6S,9S)-5,9-dihydroxy-10-((2S,3R,4S,5R)-4-hydroxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-2,4,6-trimethyl-deca-2,7-dienyl]-oxetan-2-yl}-ethyl)-2-methyl-hexa-3,5-dienyl ester
  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