(Z)-Methyl 4,6-O-isopropylidene-7-C-phenyl-L-ido-hept-2-enonate | 148162-41-8

• 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: (Z)-Methyl 4,6-O-isopropylidene-7-C-phenyl-L-ido-hept-2-enonate
• 英文别名: methyl (Z)-3-[(4S,5R,6R)-5-hydroxy-6-[(S)-hydroxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxan-4-yl]prop-2-enoate
• CAS: 148162-41-8
• 化学式: C₁₇H₂₂O₆
• 分子量: 322.358
• InChiKey: IWQRDUHMKJLUCM-XOWMOYFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-Methyl 4,6-O-isopropylidene-7-C-phenyl-L-ido-hept-2-enonate 在 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 生成 8-epi-goniotriol
  参考文献：
  名称：

  First total synthesis of potent antitumour agent (+)-goniopypyrone

  摘要：

  The structure and absolute stereochemistry of the natural goniopypyrone is confirmed as 1 by a short and stereoselective synthesis in nine steps from D-glycero-D-gulo-heptono-gamma-lactone with an overall yield of 9.7 %.

  DOI：

  10.1016/s0040-4039(00)61654-4
• 作为产物：
  描述：

  3,5-O-Isopropylidene-1,1,6-tri-C-phenyl-L-glycero-D-gulo-hexitol 在 sodium periodate 作用下， 以 甲醇 、 水 为溶剂， 生成 (Z)-Methyl 4,6-O-isopropylidene-7-C-phenyl-L-ido-hept-2-enonate
  参考文献：
  名称：

  First total synthesis of potent antitumour agent (+)-goniopypyrone

  摘要：

  The structure and absolute stereochemistry of the natural goniopypyrone is confirmed as 1 by a short and stereoselective synthesis in nine steps from D-glycero-D-gulo-heptono-gamma-lactone with an overall yield of 9.7 %.

  DOI：

  10.1016/s0040-4039(00)61654-4

文献信息

• Gonibutenolides A and B: serendipitous syntheses, relative and absolute configuration
  作者：Tony K. M. Shing、Vincent W.-F. Tai、Hon-Chung Tsui

  DOI：10.1039/c39940001293

  日期：——

  The relative and absolute stereochemistries of natural goniobutenolides A and B are established as 1 and 2 respectively by short syntheses of them and their 8-epimers.

  通过简短合成天然高尼丁内酯 A 和 B 及其 8-表聚物，确定它们的相对和绝对立体化学结构分别为 1 和 2。
• Enantiospecific Syntheses of (+)-Goniofufurone, (+)-7-epi-Goniofufurone, (+)-Goniobutenolide A, (-)-Goniobutenolide B, (+)-Goniopypyrone, (+)-Altholactone, (+)-Goniotriol, and (+)-7-Acetylgoniotriol
  作者：Tony K. M. Shing、Hon-Chung Tsui、Zhao-Hui Zhou

  DOI：10.1021/jo00115a030

  日期：1995.5

  Practical and efficient syntheses of a number of styryl lactones with various structural complexities were accomplished from commercially available and inexpensive D-glycero -D-gulo-heptono-gamma-lactone (D-glucoheptonic gamma-lactone)(11). Lactone 11 was converted by four sequential reactions (acetonation, selective deacetonation, glycol cleavage oxidation, and Grignard reaction) into key intermediates 3,5-O-isopropylidene-1, 1,6-tri-C-phenyl-D-glycero-D-gulo-hexitol (15) and 3,5-O-isopropylidene-1,1,6-tri-C-phenyl-L-glycero-D-gulo- hexitol(16). The alcohol 15 was transformed via a glycol cleavage oxidation and a Z-selective Wittig reaction into enoate Z-9 which underwent hydrolysis and an intramolecular Michael-type cyclization to give (+)-goniofufurone (1). Likewise, reaction of 16 afforded 7-epi-goniofufurone (2). Acylation and subsequent deacylation of 7-C-phenyl-D-gluco-hept-2-enono-gamma-lactone (20) readily gave (+)-goniobutenolide A (3) and (-)-goniobutenolide B (4), whereas treatment of (Z)-methyl 4,6-O-isopropylidene-7-C-phenyl-L-ido-hept-2-enonate (Z-22) with DBU followed by acid hydrolysis and intramolecular Michael reaction provided (+)-goniopypyrone (5). Mesylation of 4,6-O-isopropylidene-7-C-phenyl-L-ido-hept-2-enono-delta- lactone (27) followed by acid hydrolysis furnished (+)-altholactone (6). (+)-Goniotriol (7) and (+)-7-acetylgoniotriol (8) were readily obtained from the enoate Z-9. This work also provides a viable synthetic route for the construction of the enantiomers of the above styryl lactones for biological evaluation from the same starting material 11. Suggestions about the possible biosynthetic pathway of the styryl lactones are given.