(12S,13R)-(E)-13-acetoxy-9-oxo-12-(triisopropylsilyloxy)-10-octadecenoic acid tert-butyl ester | 537698-02-5

• 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: (12S,13R)-(E)-13-acetoxy-9-oxo-12-(triisopropylsilyloxy)-10-octadecenoic acid tert-butyl ester
• 英文别名: tert-butyl (E,12S,13R)-13-acetyloxy-9-oxo-12-tri(propan-2-yl)silyloxyoctadec-10-enoate
• CAS: 537698-02-5
• 化学式: C₃₃H₆₂O₆Si
• 分子量: 582.937
• InChiKey: ZPRRWFHHIDKLNR-QONVKJJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.26
• 重原子数：
  40
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (12S,13R)-(E)-13-acetoxy-9-oxo-12-(triisopropylsilyloxy)-10-octadecenoic acid tert-butyl ester 在 (-)-(S)-BINAL-H 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以99%的产率得到(12S,13R)-(E)-13-acetoxy-9-hydroxy-12-(triisopropylsilyloxy)-10-octadecenoic acid tert-butyl ester
  参考文献：
  名称：

  Total synthesis, elucidation of absolute stereochemistry, and adjuvant activity of trihydroxy fatty acids

  摘要：

  Pinellic acid from the tuber of Pinellia ternate, an active herbal component of the traditional Japanese herbal (Kampo) medicine Sho-seiryu-to, is a C18 trihydroxy fatty acid whose absolute stereochernistry has now been determined. All stereoisomers of pinellic acid were synthesized via regioselective asymmetric dihydroxylation, regioselective inversion, and stereoselective reduction in order to determine their absolute stereochemistries and adjuvant activities. Among this series of isomers, the (9S,12S,13S)-compound, which is a natural product, exhibited the most potent adjuvant activity. Spectral data for all of the stereoisomers of the 1,2-allylic diols were compared and related to their stereochemistries. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2006.06.088
• 作为产物：
  描述：

  tert-butyl 8-hydroxyoctanoate 在 potassium osmate(VI) 、 甲基磺酰胺 吡啶 、 咪唑 、 2,6-二甲基吡啶 、 正丁基锂 、 mercury(II) perchlorate 、 18-冠醚-6 、 碘 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 三苯基膦 、 calcium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 、 苯 为溶剂， 反应 107.66h， 生成 (12S,13R)-(E)-13-acetoxy-9-oxo-12-(triisopropylsilyloxy)-10-octadecenoic acid tert-butyl ester
  参考文献：
  名称：

  Total synthesis, elucidation of absolute stereochemistry, and adjuvant activity of trihydroxy fatty acids

  摘要：

  Pinellic acid from the tuber of Pinellia ternate, an active herbal component of the traditional Japanese herbal (Kampo) medicine Sho-seiryu-to, is a C18 trihydroxy fatty acid whose absolute stereochernistry has now been determined. All stereoisomers of pinellic acid were synthesized via regioselective asymmetric dihydroxylation, regioselective inversion, and stereoselective reduction in order to determine their absolute stereochemistries and adjuvant activities. Among this series of isomers, the (9S,12S,13S)-compound, which is a natural product, exhibited the most potent adjuvant activity. Spectral data for all of the stereoisomers of the 1,2-allylic diols were compared and related to their stereochemistries. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2006.06.088

文献信息

• Total synthesis and adjuvant activity of all stereoisomers of pinellic acid
  作者：Tatsuya Shirahata、Toshiaki Sunazuka、Kiminari Yoshida、Daisuke Yamamoto、Yoshihiko Harigaya、Takayuki Nagai、Hiroaki Kiyohara、Haruki Yamada、Isao Kuwajima、Satoshi Ōmura

  DOI：10.1016/s0960-894x(02)01069-7

  日期：2003.3

  Pinellic acid is a novel and potentially useful oral adjuvant when used in conjunction with intranasal inoculation of influenza HA vaccines. All stereoisomers of pinellic acid have been synthesized via regioselective asymmetric dihydroxylation, regioselective inversion, and stereoselective reduction, and their adjuvant activities were characterized. Among this series of isomers, 9S, 12S, 13S compound

  松果酸与鼻内接种HA流感疫苗一起使用时，是一种新颖且可能有用的口服佐剂。已通过区域选择性不对称二羟基化，区域选择性反转和立体选择性还原合成了所有松果酸立体异构体，并对其佐剂活性进行了表征。在这一系列异构体中，9S，12S，13S化合物具有最强的佐剂活性。讨论了构效关系。