(E)-(4R,5S)-4-Benzyloxy-5-[(E)-(4R,5S)-4-benzyloxy-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid | 294198-67-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E)-(4R,5S)-4-Benzyloxy-5-[(E)-(4R,5S)-4-benzyloxy-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid
• CAS: 294198-67-7
• 化学式: C₃₀H₃₆O₉
• 分子量: 540.61
• InChiKey: MPNSUDPQTXPYKP-VUDNUXHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  39.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  128.59
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (E)-(4R,5S)-4-Benzyloxy-5-[(E)-(4R,5S)-4-benzyloxy-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid 在 4 A molecular sieve 、 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 26.0h， 生成 (7E,13E)-(4R,9R,10S,15R,16S)-9,15-Bis-benzyloxy-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione
  参考文献：
  名称：

  Total syntheses of macrosphelides (+)-A, (−)-A and (+)-E

  摘要：

  Total syntheses of (+)-macrosphelide A 1 (18.5% overall yield in 11 steps) and (+)-macrosphelide E 2 (23.9% overall yield in 11 steps) have been achieved via the chemoenzymatic reaction product (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate 4. The enantiomer (-)-A (1) (14.2% overall yield in 11 steps) of (+)-1 was also synthesized from the chemoenzymatic reaction product (4S,SR)-4-benzyloxy-5-hydroxy-2(E)hexenoate 4. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00245-7
• 作为产物：
  描述：

  (E)-(4R,5S)-4-Benzyloxy-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester 在 AcOH-AcONa buffer 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 (E)-(4R,5S)-4-Benzyloxy-5-[(E)-(4R,5S)-4-benzyloxy-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid
  参考文献：
  名称：

  Total syntheses of macrosphelides (+)-A, (−)-A and (+)-E

  摘要：

  Total syntheses of (+)-macrosphelide A 1 (18.5% overall yield in 11 steps) and (+)-macrosphelide E 2 (23.9% overall yield in 11 steps) have been achieved via the chemoenzymatic reaction product (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate 4. The enantiomer (-)-A (1) (14.2% overall yield in 11 steps) of (+)-1 was also synthesized from the chemoenzymatic reaction product (4S,SR)-4-benzyloxy-5-hydroxy-2(E)hexenoate 4. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00245-7