8-[2-((E)-(3R,4R)-4-Hydroxy-3-triisopropylsilanyloxy-non-1-enyl)-[1,3]dithian-2-yl]-octanoic acid tert-butyl ester | 401901-50-6

• 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: 8-[2-((E)-(3R,4R)-4-Hydroxy-3-triisopropylsilanyloxy-non-1-enyl)-[1,3]dithian-2-yl]-octanoic acid tert-butyl ester
• 英文别名: tert-butyl 8-[2-[(E,3R,4R)-4-hydroxy-3-tri(propan-2-yl)silyloxynon-1-enyl]-1,3-dithian-2-yl]octanoate
• CAS: 401901-50-6
• 化学式: C₃₄H₆₆O₄S₂Si
• 分子量: 631.113
• InChiKey: JOIKKIODSDWPCK-AOMQEVRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.68
• 重原子数：
  41
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-[2-((E)-(3R,4R)-4-Hydroxy-3-triisopropylsilanyloxy-non-1-enyl)-[1,3]dithian-2-yl]-octanoic acid tert-butyl ester 在 吡啶 、 18-冠醚-6 、 potassium tert-butylate 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 叔丁醇 、 苯 为溶剂， 反应 54.0h， 生成 8-[2-((E)-(3R,4S)-3,4-Dihydroxy-non-1-enyl)-[1,3]dithian-2-yl]-octanoic 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：

  辛二酸单甲酯 在 potassium osmate(VI) 、 甲基磺酰胺 咪唑 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 正丁基锂 、 硼烷四氢呋喃络合物 、 二碳酸二叔丁酯 、 碘 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 三苯基膦 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 138.58h， 生成 8-[2-((E)-(3R,4R)-4-Hydroxy-3-triisopropylsilanyloxy-non-1-enyl)-[1,3]dithian-2-yl]-octanoic 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, elucidation of absolute stereochemistry, and adjuvant activity of trihydroxy fatty acids
  作者：Tatsuya Shirahata、Toshiaki Sunazuka、Kiminari Yoshida、Daisuke Yamamoto、Yoshihiro Harigaya、Isao Kuwajima、Takayuki Nagai、Hiroaki Kiyohara、Haruki Yamada、Satoshi Ōmura

  DOI：10.1016/j.tet.2006.06.088

  日期：2006.10

  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.