(2R,3S,4S,5R,6S)-3,4,5,6-tetrahydro-5-(4-methoxybenzyloxy)-2,4,6-trimethyl-2-vinyl-2H-pyran-3-ol | 1039034-35-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S,4S,5R,6S)-3,4,5,6-tetrahydro-5-(4-methoxybenzyloxy)-2,4,6-trimethyl-2-vinyl-2H-pyran-3-ol
• 英文别名: (2R,3S,4S,5R,6S)-2-ethenyl-5-[(4-methoxyphenyl)methoxy]-2,4,6-trimethyloxan-3-ol
• CAS: 1039034-35-9
• 化学式: C₁₈H₂₆O₄
• 分子量: 306.402
• InChiKey: AXUJCHWQLVJUQP-FRULXJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6S)-3,4,5,6-tetrahydro-5-(4-methoxybenzyloxy)-2,4,6-trimethyl-2-vinyl-2H-pyran-3-ol 、 2-溴丙酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 以77%的产率得到(2R,3S,4R,5R,6S)-3,4,5,6-tetrahydro-3-(2-bromopropanoyloxy)-5-(4-methoxybenzyloxy)-2,4,6-trimethyl-2-vinyl-2H-pyran
  参考文献：
  名称：

  Asymmetric Total Synthesis of Botcinins C, D, and F

  摘要：

  Stereoselective total synthesis of botcinins C, D, and F is effectively carried out through asymmetric aldol reactions, 6-endo ring closure, and Sml(12)-mediated 3,4-trans or -cis stereoselective intramolecular Reformatsky reaction. Rapid esterification of the main skeleton of botcinins with the chiral side chain using MNBA and DMAP produced botcinin D, an antifungal chemical against a pathogen of rice blast disease.

  DOI：

  10.1021/ol801066y
• 作为产物：
  描述：

  (3R,4R,5R,6R,7S)-7-(tert-butyldimethylsiloxy)-6-(4-methoxybenzyloxy)-3,5-dimethyl-3,4-epoxy-1-octene 在 四丁基氟化铵 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 以96%的产率得到(2R,3S,4S,5R,6S)-3,4,5,6-tetrahydro-5-(4-methoxybenzyloxy)-2,4,6-trimethyl-2-vinyl-2H-pyran-3-ol
  参考文献：
  名称：

  Asymmetric Total Synthesis of Botcinins C, D, and F

  摘要：

  Stereoselective total synthesis of botcinins C, D, and F is effectively carried out through asymmetric aldol reactions, 6-endo ring closure, and Sml(12)-mediated 3,4-trans or -cis stereoselective intramolecular Reformatsky reaction. Rapid esterification of the main skeleton of botcinins with the chiral side chain using MNBA and DMAP produced botcinin D, an antifungal chemical against a pathogen of rice blast disease.

  DOI：

  10.1021/ol801066y

文献信息

• Asymmetric total synthesis of botcinic acid and its derivatives: synthetic revision of the structure of botcinolides
  作者：Hiroki Fukui、Seiichi Hitomi、Ryo-suke Suzuki、Tatsuhiko Ikeda、Yuma Umezaki、Keisuke Tsuji、Isamu Shiina

  DOI：10.1016/j.tetlet.2008.08.108

  日期：2008.11

  The stereoselective total syntheses of botcinic acid, botcinic acid methyl ester, 3-O-acetylbotcinic acid methyl ester, botcineric acid, and botcinin E were achieved. The structures of these compounds have been unequivocally determined through their total synthesis, and they are identified with the revised structures of botcinolide, 4-O-methylbotcinolide, 3-O-acetyl-5-O-methylbotcinolide, homobotcinolide

  得到了立体选择性的植物酸，植物酸甲酯，3- O-乙酰基植物酸甲酯，植物酸和植物素E的全合成。这些化合物的结构已通过它们的全合成明确确定，并已通过肉毒杆菌内酯，4- O-甲基肉毒酚，3- O-乙酰基-5- O-甲基肉毒杆菌素，高肉毒酚和2-表肉毒酚内酯的修饰结构进行鉴定，分别。
• Asymmetric Total Synthesis of Botcinins C, D, and F
  作者：Hiroki Fukui、Isamu Shiina

  DOI：10.1021/ol801066y

  日期：2008.7.17

  Stereoselective total synthesis of botcinins C, D, and F is effectively carried out through asymmetric aldol reactions, 6-endo ring closure, and Sml(12)-mediated 3,4-trans or -cis stereoselective intramolecular Reformatsky reaction. Rapid esterification of the main skeleton of botcinins with the chiral side chain using MNBA and DMAP produced botcinin D, an antifungal chemical against a pathogen of rice blast disease.