(E)-(S)-5-[(R)-3-(Tetrahydro-pyran-2-yloxy)-hex-5-enoyloxy]-hex-2-enoic acid (S)-1-furan-2-yl-ethyl ester | 458564-66-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-(S)-5-[(R)-3-(Tetrahydro-pyran-2-yloxy)-hex-5-enoyloxy]-hex-2-enoic acid (S)-1-furan-2-yl-ethyl ester
• 英文别名: [(1S)-1-(furan-2-yl)ethyl] (E,5S)-5-[(3R)-3-(oxan-2-yloxy)hex-5-enoyl]oxyhex-2-enoate
• CAS: 458564-66-4
• 化学式: C₂₃H₃₂O₇
• 分子量: 420.503
• InChiKey: IHJKZNWHWVYBJX-BZEZQURCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  84.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-(S)-5-[(R)-3-(Tetrahydro-pyran-2-yloxy)-hex-5-enoyloxy]-hex-2-enoic acid (S)-1-furan-2-yl-ethyl ester 在 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 以75%的产率得到(E)-(S)-5-((R)-3-Hydroxy-hex-5-enoyloxy)-hex-2-enoic acid (S)-1-furan-2-yl-ethyl ester
  参考文献：
  名称：

  Synthesis of macrosphelides H and G

  摘要：

  A compound with furyl and vinyl groups was designed as an intermediate for synthesis of macrosphelide H. The furyl group was oxidatively transformed into the key C(5)-O(10) part by a two-step conversion of (1) NBS, H2O: (2) NaClO2 without affecting the free hydroxyl group at C(3). thus furnishing the seco acid, while the Wacker oxidation at the final step was used to convert the vinyl group into acetyl group to afford macrosphelide H. This strategy was applied successfully to synthesis or macrosphelide G as well. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00781-5
• 作为产物：
  描述：

  (5S,2E)-5-tetrahydropyranyloxy-2-hexenoic acid 在 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 、 4-甲基苯磺酸吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (E)-(S)-5-[(R)-3-(Tetrahydro-pyran-2-yloxy)-hex-5-enoyloxy]-hex-2-enoic acid (S)-1-furan-2-yl-ethyl ester
  参考文献：
  名称：

  Synthesis of macrosphelides H and G

  摘要：

  A compound with furyl and vinyl groups was designed as an intermediate for synthesis of macrosphelide H. The furyl group was oxidatively transformed into the key C(5)-O(10) part by a two-step conversion of (1) NBS, H2O: (2) NaClO2 without affecting the free hydroxyl group at C(3). thus furnishing the seco acid, while the Wacker oxidation at the final step was used to convert the vinyl group into acetyl group to afford macrosphelide H. This strategy was applied successfully to synthesis or macrosphelide G as well. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00781-5

文献信息

• Synthesis of macrosphelides H and G
  作者：Yuichi Kobayashi、Yong-Gang Wang

  DOI：10.1016/s0040-4039(02)00781-5

  日期：2002.6

  A compound with furyl and vinyl groups was designed as an intermediate for synthesis of macrosphelide H. The furyl group was oxidatively transformed into the key C(5)-O(10) part by a two-step conversion of (1) NBS, H2O: (2) NaClO2 without affecting the free hydroxyl group at C(3). thus furnishing the seco acid, while the Wacker oxidation at the final step was used to convert the vinyl group into acetyl group to afford macrosphelide H. This strategy was applied successfully to synthesis or macrosphelide G as well. (C) 2002 Elsevier Science Ltd. All rights reserved.