(3E,5R,6S)-8-(benzyloxy)-6-hydroxy-5-methyloct-3-enoic acid methyl ester | 781642-34-0

• 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: (3E,5R,6S)-8-(benzyloxy)-6-hydroxy-5-methyloct-3-enoic acid methyl ester
• CAS: 781642-34-0
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: LOFHYHIBPKNJAR-LREFGLRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  21.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3E,5R,6S)-8-(benzyloxy)-6-hydroxy-5-methyloct-3-enoic acid methyl ester 在 吡啶 、 臭氧 、 二甲基硫 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Total Synthesis of Basiliskamides A and B

  摘要：

  The first enantioselective synthesis of the polyketide antibiotics basiliskamides A and B, which exhibit potent in vivo activity against Candida albicans and Aspergillus fumigatus, has been achieved. Serial asymmetric crotylsilane and crotylboronate additions established the C7-C10 stereochemical tetrad. Takai iodoolefination and palladium-mediated cross-coupling were used to install the (Z,E)-vinyl acrylamide. Spectroscopic data is consistent with the assignment of the absolute configurations of the natural products as (7S,8S,9R,10S).

  DOI：

  10.1021/ol048574m
• 作为产物：
  描述：

  3-苄氧基丙醛 、 (E)-(3R)-Methyl 3-(dimethylphenylsilyl)hex-4-enoate 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以74%的产率得到(3E,5R,6S)-8-(benzyloxy)-6-hydroxy-5-methyloct-3-enoic acid methyl ester
  参考文献：
  名称：

  Total Synthesis of Basiliskamides A and B

  摘要：

  The first enantioselective synthesis of the polyketide antibiotics basiliskamides A and B, which exhibit potent in vivo activity against Candida albicans and Aspergillus fumigatus, has been achieved. Serial asymmetric crotylsilane and crotylboronate additions established the C7-C10 stereochemical tetrad. Takai iodoolefination and palladium-mediated cross-coupling were used to install the (Z,E)-vinyl acrylamide. Spectroscopic data is consistent with the assignment of the absolute configurations of the natural products as (7S,8S,9R,10S).

  DOI：

  10.1021/ol048574m