(5R,6R,7R,8R)-6,7-O-isopropylidene-5,6,7,8-dodecanetetraol | 142285-54-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5R,6R,7R,8R)-6,7-O-isopropylidene-5,6,7,8-dodecanetetraol
• 英文别名: (1R)-1-[(4R,5R)-5-[(1R)-1-hydroxypentyl]-2,2-dimethyl-1,3-dioxolan-4-yl]pentan-1-ol
• CAS: 142285-54-9
• 化学式: C₁₅H₃₀O₄
• 分子量: 274.401
• InChiKey: RUXCHJAOKMEAQR-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5R,6R,7R,8R)-6,7-O-isopropylidene-5,6,7,8-dodecanetetraol 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 生成 (5R,6S,7S,8R)-5,8-di-O-methanesulfonyl-5,6,7,8-dodecanetetraol
  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：

  溴丙烷 、 1,2;5,6-dianhydro-3,4-O-isopropylidene-D-mannitol 在 magnesium 、 1,2-二溴乙烷 、 copper(I) bromide dimethylsulfide complex 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 反应 0.5h， 以79%的产率得到(5R,6R,7R,8R)-6,7-O-isopropylidene-5,6,7,8-dodecanetetraol
  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

文献信息

• <scp>d</scp>-Mannitol as the Chiral Source for the EPC Synthesis of Both Enantiomers of 3-Ethoxycarbonyl-4-hydroxy-2-isoxazolines and Highly Functionalized Tricyclic Systems
  作者：Emanuela Marotta、Marco Baravelli、Luigi Maini、Paolo Righi、Goffredo Rosini

  DOI：10.1021/jo980941i

  日期：1998.11.1

  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.