(2S,3S,4R,5R,6S)-3,4,5,6-tetrahydro-3-(2-bromopropanoyloxy)-2-formyl-5-(4-methoxybenzyloxy)-2,4,6-trimethyl-2H-pyran | 1039034-36-0

• 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: (2S,3S,4R,5R,6S)-3,4,5,6-tetrahydro-3-(2-bromopropanoyloxy)-2-formyl-5-(4-methoxybenzyloxy)-2,4,6-trimethyl-2H-pyran
• 英文别名: [(2S,3S,4R,5R,6S)-2-formyl-5-[(4-methoxyphenyl)methoxy]-2,4,6-trimethyloxan-3-yl] 2-bromopropanoate
• CAS: 1039034-36-0
• 化学式: C₂₀H₂₇BrO₆
• 分子量: 443.335
• InChiKey: CIDFUMLQIYDSEU-VWSQRDSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R,6S)-3,4,5,6-tetrahydro-3-(2-bromopropanoyloxy)-2-formyl-5-(4-methoxybenzyloxy)-2,4,6-trimethyl-2H-pyran 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (3S,4R,4aR,6S,7R,8R,8aS)-3,4,4a,7,8,8a-hexahydro-4-hydroxy-7-(4-methoxybenzyloxy)-3,4a,6,8-tetramethylpyrano[3,2-b]pyran-2(3H)-one 、 (3R,4R,4aR,6S,7R,8R,8aS)-3,4,4a,7,8,8a-hexahydro-4-hydroxy-7-(4-methoxybenzyloxy)-3,4a,6,8-tetramethylpyrano[3,2-b]pyran-2(3H)-one
  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：

  (2R,3S,4R,5R,6S)-3,4,5,6-tetrahydro-3-(2-bromopropanoyloxy)-5-(4-methoxybenzyloxy)-2,4,6-trimethyl-2-vinyl-2H-pyran 在 臭氧 、 三苯基膦 作用下， 以 甲醇 为溶剂， 反应 1.75h， 以87%的产率得到(2S,3S,4R,5R,6S)-3,4,5,6-tetrahydro-3-(2-bromopropanoyloxy)-2-formyl-5-(4-methoxybenzyloxy)-2,4,6-trimethyl-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

文献信息

• 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.