(6R,7S,8S,9R)-6,9-di-O-(methanesulfonyl)tetradecane-1,13-diene-6,7,8,9-tetraol | 216855-00-4

• 英文名称: (6R,7S,8S,9R)-6,9-di-O-(methanesulfonyl)tetradecane-1,13-diene-6,7,8,9-tetraol
• 英文别名: [(6R,7S,8S,9R)-7,8-dihydroxy-9-methylsulfonyloxytetradeca-1,13-dien-6-yl] methanesulfonate
• CAS: 216855-00-4
• 化学式: C₁₆H₃₀O₈S₂
• 分子量: 414.541
• InChiKey: YXRKWHDBMUMASM-KLHDSHLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.11
• 重原子数：
  26.0
• 可旋转键数：
  15.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  127.2
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (6R,7S,8S,9R)-6,9-di-O-(methanesulfonyl)tetradecane-1,13-diene-6,7,8,9-tetraol 在 咪唑 、 sodium periodate 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 ethyl (2aR,6S,6aS,6bR)-2,2-dimethyl-6-(4-pentenyl)tetrahydro-2H,6bH-1,4,5-trioxa-4a-aza-2-silacyclopenta[cd]pentalene-6b-carboxylate
  参考文献：
  名称：

  d-Mannitol as the Chiral Source for the EPC Synthesis of Both Enantiomers of 3-Ethoxycarbonyl-4-hydroxy-2-isoxazolines and Highly Functionalized Tricyclic Systems

  摘要：

  The EPC preparation of both enantiomers of cis- and trans 5-substituted 4-hydroxy-2-isoxazoline 2-oxides has been achieved in an enantiodivergent fashion starting from D-mannitol through the application of the tandem nitroaldol-cyclization reaction to enantiomerically pure alpha-mesyloxyaldehydes. These stereochemically labile aldehydes have been generated in situ and reacted under very mild domino conditions. Enantiomeric purity of the products has been assessed by H-1 NMR and HPLC analyses of the corresponding Mosher's esters. The enantiomerically pure 4-hydroxy-2-isoxazoline a-oxides have been employed as pivotal intermediates for the EPC preparation of the corresponding deoxygenated derivatives and highly functionalized tricyclic systems (HFTS) 1, useful for the preparation of 2-aminopolyols and alpha,alpha-disubstituted polyhydroxy amino acids.

  DOI：

  10.1021/jo980941i
• 作为产物：
  描述：

  1,2;5,6-dianhydro-3,4-O-isopropylidene-D-mannitol 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 magnesium 、 1,2-二溴乙烷 作用下， 以 乙醚 、 溶剂黄146 为溶剂， 反应 1.5h， 生成 (6R,7S,8S,9R)-6,9-di-O-(methanesulfonyl)tetradecane-1,13-diene-6,7,8,9-tetraol
  参考文献：
  名称：

  d-Mannitol as the Chiral Source for the EPC Synthesis of Both Enantiomers of 3-Ethoxycarbonyl-4-hydroxy-2-isoxazolines and Highly Functionalized Tricyclic Systems

  摘要：

  The EPC preparation of both enantiomers of cis- and trans 5-substituted 4-hydroxy-2-isoxazoline 2-oxides has been achieved in an enantiodivergent fashion starting from D-mannitol through the application of the tandem nitroaldol-cyclization reaction to enantiomerically pure alpha-mesyloxyaldehydes. These stereochemically labile aldehydes have been generated in situ and reacted under very mild domino conditions. Enantiomeric purity of the products has been assessed by H-1 NMR and HPLC analyses of the corresponding Mosher's esters. The enantiomerically pure 4-hydroxy-2-isoxazoline a-oxides have been employed as pivotal intermediates for the EPC preparation of the corresponding deoxygenated derivatives and highly functionalized tricyclic systems (HFTS) 1, useful for the preparation of 2-aminopolyols and alpha,alpha-disubstituted polyhydroxy amino acids.

  DOI：

  10.1021/jo980941i