5-((S)-3-Methoxymethoxy-hexylsulfanyl)-1-phenyl-1H-tetrazole | 910030-50-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-((S)-3-Methoxymethoxy-hexylsulfanyl)-1-phenyl-1H-tetrazole
• CAS: 910030-50-1
• 化学式: C₁₅H₂₂N₄O₂S
• 分子量: 322.431
• InChiKey: XSJOHPJYPOOJCB-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  22.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  62.06
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-((S)-3-Methoxymethoxy-hexylsulfanyl)-1-phenyl-1H-tetrazole 在 palladium on activated charcoal 四丁基氟化铵 、 氢气 、 sodium hexamethyldisilazane 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 81.5h， 生成 (2S,3R,4aS,5S,8aR)-1-(tert-butoxycarbonyl)-2-methyl-3-hydroxy-5-[(5S)-5-(methoxymethoxy)octan-1-yl]decahydroquinoline
  参考文献：
  名称：

  Facile Entry to Substituted Decahydroquinoline Alkaloids. Total Synthesis of Lepadins A−E and H

  摘要：

  Condensation of a L-alanine derived delta-bromo-beta-silyloxy-propylamine with 1,3-cyclohexadione followed by alkylative cyclization produces a bicyclic enone. Diastereoselective Pt/C-catalyzed hydrogenation of this enone in HOAc provides a 5-oxo-cis-fused decahydroquinoline. Wittig olefination of this decahydroquinoline and subsequent epimerization of the resulting 5-formyl intermediate gives rise to a 5-beta-formyl decahydroquinoline exclusively. In a parallel procedure, Peterson reaction of this decahydroquinoline and subsequent hydrogenation of the generated 5-exo-olefin provides a decahydroquinoline with a 5-alpha-substituent predominantly. For these two diastereoselective processes, using the intermediates without N-protection as the substrates is essential because the corresponding N-Boc intermediates give poor diastereoselectivity. The intermediate with beta-form side chain is further converted into lepadins A-C via carbon chain elongation, while the intermediate with alpha-form side chain is transformed into lepadins D, E, and H and corresponding 5'-epimers via connection with two sulfones generated from two Sharpless epoxidation products. By comparison of the rotations and NMR data, the stereochemistry of lepadins D, E, and H is assigned as 2S, 3R, 4aS, 5S, 8aR, 5'R.

  DOI：

  10.1021/jo061070c
• 作为产物：
  描述：

  tert-Butyl-((S)-3-methoxymethoxy-hexyloxy)-diphenyl-silane 在 三丁基膦 、 四丁基氟化铵 、 偶氮二甲酸二乙酯 作用下， 生成 5-((S)-3-Methoxymethoxy-hexylsulfanyl)-1-phenyl-1H-tetrazole
  参考文献：
  名称：

  Facile Entry to Substituted Decahydroquinoline Alkaloids. Total Synthesis of Lepadins A−E and H

  摘要：

  Condensation of a L-alanine derived delta-bromo-beta-silyloxy-propylamine with 1,3-cyclohexadione followed by alkylative cyclization produces a bicyclic enone. Diastereoselective Pt/C-catalyzed hydrogenation of this enone in HOAc provides a 5-oxo-cis-fused decahydroquinoline. Wittig olefination of this decahydroquinoline and subsequent epimerization of the resulting 5-formyl intermediate gives rise to a 5-beta-formyl decahydroquinoline exclusively. In a parallel procedure, Peterson reaction of this decahydroquinoline and subsequent hydrogenation of the generated 5-exo-olefin provides a decahydroquinoline with a 5-alpha-substituent predominantly. For these two diastereoselective processes, using the intermediates without N-protection as the substrates is essential because the corresponding N-Boc intermediates give poor diastereoselectivity. The intermediate with beta-form side chain is further converted into lepadins A-C via carbon chain elongation, while the intermediate with alpha-form side chain is transformed into lepadins D, E, and H and corresponding 5'-epimers via connection with two sulfones generated from two Sharpless epoxidation products. By comparison of the rotations and NMR data, the stereochemistry of lepadins D, E, and H is assigned as 2S, 3R, 4aS, 5S, 8aR, 5'R.

  DOI：

  10.1021/jo061070c