(5R)-2-[(3S,4R,5S,8S)-4-hydroxy-8-methoxy-3,5-dimethyl-8-(3-phenylmethoxyphenyl)oct-1-ynyl]-3,3,5-trimethyl-6-oxocyclohexene-1-carboxylic acid | 165069-63-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5R)-2-[(3S,4R,5S,8S)-4-hydroxy-8-methoxy-3,5-dimethyl-8-(3-phenylmethoxyphenyl)oct-1-ynyl]-3,3,5-trimethyl-6-oxocyclohexene-1-carboxylic acid
• CAS: 165069-63-6
• 化学式: C₃₄H₄₂O₆
• 分子量: 546.704
• InChiKey: WXPVMBMNBPBCMN-PGSUIMDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (5R)-2-[(3S,4R,5S,8S)-4-hydroxy-8-methoxy-3,5-dimethyl-8-(3-phenylmethoxyphenyl)oct-1-ynyl]-3,3,5-trimethyl-6-oxocyclohexene-1-carboxylic acid 以 乙醚 为溶剂， 生成 (R)-2-[(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-4-hydroxy-8-methoxy-3,5-dimethyl-oct-1-ynyl]-3,3,5-trimethyl-6-oxo-cyclohex-1-enecarboxylic acid methyl ester
  参考文献：
  名称：

  Synthetic study on oscillatoxin D: Construction of the C1–C26 spiroether segment by intramolecular aldol condensation and Michael-type addition

  摘要：

  The C-1-C-7 segment (10) and the C-8-C-21 segment (14) of oscillatoxin D have been synthesized efficiently. The acyclic compound obtained by coupling of these two segments, has been converted int the C-1-C-26 spiroether (18) possessing the same stereogenic centers of oscillatoxin D. The construction of the spiroether has been achieved by intramolecular aldol condensation and Michael-type addition as key steps.

  DOI：

  10.1016/s0040-4039(00)73355-7
• 作为产物：
  描述：

  tert-Butyl-((R)-4-[1,3]dithian-2-yl-2,2-dimethyl-pentyloxy)-diphenyl-silane 在 sodium chlorite 、 sodium dihydrogenphosphate 、 N-氯代丁二酰亚胺 、 正丁基锂 、 2-甲基-2-丁烯 、 pyridine-SO3 complex 、 四丁基氟化铵 、 水 、 叔丁基锂 、 silver nitrate 、 二甲基亚砜 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 、 氯仿 、 水 、 乙腈 、 叔丁醇 为溶剂， 生成 (5R)-2-[(3S,4R,5S,8S)-4-hydroxy-8-methoxy-3,5-dimethyl-8-(3-phenylmethoxyphenyl)oct-1-ynyl]-3,3,5-trimethyl-6-oxocyclohexene-1-carboxylic acid
  参考文献：
  名称：

  Synthetic study on oscillatoxin D: Construction of the C1–C26 spiroether segment by intramolecular aldol condensation and Michael-type addition

  摘要：

  The C-1-C-7 segment (10) and the C-8-C-21 segment (14) of oscillatoxin D have been synthesized efficiently. The acyclic compound obtained by coupling of these two segments, has been converted int the C-1-C-26 spiroether (18) possessing the same stereogenic centers of oscillatoxin D. The construction of the spiroether has been achieved by intramolecular aldol condensation and Michael-type addition as key steps.

  DOI：

  10.1016/s0040-4039(00)73355-7

文献信息

• Total syntheses of oscillatoxin D and 30-methyloscillatoxin D
  作者：Hiroaki Toshima、Takashi Goto、Akitami Ichihara

  DOI：10.1016/0040-4039(95)00544-m

  日期：1995.5

  The first total syntheses of oscillatoxin D (1a) and 30-methyloscillatoxin D (1b) have been accomplished. The construction of the spiroether has been achieved by intramolecular Michael-type addition as a key step based on a possible biomimetic pathway.