(E,4R,5S)-5-[(E,4R,5S)-5-[(3S)-3-hydroxybutanoyl]oxy-4-phenylmethoxyhex-2-enoyl]oxy-4-phenylmethoxyhex-2-enoic acid | 294198-56-4

• 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)-5-[(E,4R,5S)-5-[(3S)-3-hydroxybutanoyl]oxy-4-phenylmethoxyhex-2-enoyl]oxy-4-phenylmethoxyhex-2-enoic acid
• CAS: 294198-56-4
• 化学式: C₃₀H₃₆O₉
• 分子量: 540.61
• InChiKey: MPNSUDPQTXPYKP-LIBVWABZSA-N

物化性质

• 沸点：
  688.0±55.0 °C(predicted)
• 密度：
  1.206±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  39
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (E,4R,5S)-5-[(E,4R,5S)-5-[(3S)-3-hydroxybutanoyl]oxy-4-phenylmethoxyhex-2-enoyl]oxy-4-phenylmethoxyhex-2-enoic acid 在 三氯化铝 、 4 A molecular sieve 、 2,4,6-三氯苯甲酰氯 、 三乙胺 、 间二甲苯 作用下， 以 二氯甲烷 为溶剂， 反应 29.0h， 生成 macrosphelide E
  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,2S,3R)-6-oxo-3-phenylmethoxy-6-(2,2,2-trichloroethoxy)hex-4-en-2-yl] (E,4R,5S)-5-[(3S)-3-[tert-butyl(dimethyl)silyl]oxybutanoyl]oxy-4-phenylmethoxyhex-2-enoate 在 AcOH-AcONa buffer 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 (E,4R,5S)-5-[(E,4R,5S)-5-[(3S)-3-hydroxybutanoyl]oxy-4-phenylmethoxyhex-2-enoyl]oxy-4-phenylmethoxyhex-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

文献信息

• Total syntheses of macrosphelides (+)-A, (−)-A and (+)-E
  作者：Machiko Ono、Hiroshi Nakamura、Fumi Konno、Hiroyuki Akita

  DOI：10.1016/s0957-4166(00)00245-7

  日期：2000.7

  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.