(-)-(1'R,2'S,4S,5S)-4-<2'-(Benzyloxy)-1',3'dimethylbut-3-enyl>-2,2,5-trimethyl-1,3-dioxane | 161317-43-7

• 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: (-)-(1'R,2'S,4S,5S)-4-<2'-(Benzyloxy)-1',3'dimethylbut-3-enyl>-2,2,5-trimethyl-1,3-dioxane
• 英文别名: (4S,5S)-2,2,5-trimethyl-4-[(2R,3S)-4-methyl-3-phenylmethoxypent-4-en-2-yl]-1,3-dioxane
• CAS: 161317-43-7
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: RNTZJCLAVYWRRI-DKKFBQAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(1'R,2'S,4S,5S)-4-<2'-(Benzyloxy)-1',3'dimethylbut-3-enyl>-2,2,5-trimethyl-1,3-dioxane 在 四丙基高钌酸铵 、 二异丁基氢化铝 、 氧化-4-甲基吗啉一水合物 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.25h， 生成 (-)-(2R,3R,4R,5S)-5-(Benzyloxy)-3-(isopropyloxy)-2,4-dimethylhept-6-enal
  参考文献：
  名称：

  A New Stereoselective and Convergent Approach to the Synthesis of Long-Chain Polypropionate Fragments

  摘要：

  Optically pure Diels-Alder adducts of 2,4-dimethylfuran and 1-cyanovinyl (1'R)- or (1'S)-camphanate are obtained readily. These 1,5-dimethyl-7-oxabicyclo[2.2.1]hept-5-en-1-yl derivatives can be converted with high stereoselectivity into polypropionate fragments such as (-)-(2R,3R,4R,5S)-5-(benzyloxy)-3-(isopropyloxy)-2,4-dimethylhept-6-enal ((-)-16) or (-)-(2R,2'S,3'S,4'S,5'S)-2-[4-(benzyloxy)tetrahydro-3,5-dimethyl-5-methoxyfur-2-yl]propanal ((-)-20). The latter underwent stereoselective cross-aldolization with the lithium enolate of (+)-(1S,4S,5S,6S)-6-exo-(benzyloxy)-1,5-endo-dimethyl-7-oxabicyclo[2.2.1]heptan-2-one ((+)-9) giving an aldol ((-)-23); like mode of aldolization) that can be converted into a polypropionate fragment containing nine contiguous stereogenic centers.

  DOI：

  10.1021/jo00099a020
• 作为产物：
  描述：

  (+)-(1S,4R,5S,6S,7S)-7-exo-(Benzyloxy)-1,4-exo,6-endo-trimethyl-2,8-dioxabicyclo<3.2.1>octan-3-one 在 lithium aluminium tetrahydride 、 molecular sieve 、 四丙基高钌酸铵 、 sodium amide 、 氧化-4-甲基吗啉一水合物 、 tin(ll) chloride 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.83h， 生成 (-)-(1'R,2'S,4S,5S)-4-<2'-(Benzyloxy)-1',3'dimethylbut-3-enyl>-2,2,5-trimethyl-1,3-dioxane
  参考文献：
  名称：

  A New Stereoselective and Convergent Approach to the Synthesis of Long-Chain Polypropionate Fragments

  摘要：

  Optically pure Diels-Alder adducts of 2,4-dimethylfuran and 1-cyanovinyl (1'R)- or (1'S)-camphanate are obtained readily. These 1,5-dimethyl-7-oxabicyclo[2.2.1]hept-5-en-1-yl derivatives can be converted with high stereoselectivity into polypropionate fragments such as (-)-(2R,3R,4R,5S)-5-(benzyloxy)-3-(isopropyloxy)-2,4-dimethylhept-6-enal ((-)-16) or (-)-(2R,2'S,3'S,4'S,5'S)-2-[4-(benzyloxy)tetrahydro-3,5-dimethyl-5-methoxyfur-2-yl]propanal ((-)-20). The latter underwent stereoselective cross-aldolization with the lithium enolate of (+)-(1S,4S,5S,6S)-6-exo-(benzyloxy)-1,5-endo-dimethyl-7-oxabicyclo[2.2.1]heptan-2-one ((+)-9) giving an aldol ((-)-23); like mode of aldolization) that can be converted into a polypropionate fragment containing nine contiguous stereogenic centers.

  DOI：

  10.1021/jo00099a020

文献信息

• A New Stereoselective and Convergent Approach to the Synthesis of Long-Chain Polypropionate Fragments
  作者：Anne-Francoise Sevin、Pierre Vogel

  DOI：10.1021/jo00099a020

  日期：1994.10

  Optically pure Diels-Alder adducts of 2,4-dimethylfuran and 1-cyanovinyl (1'R)- or (1'S)-camphanate are obtained readily. These 1,5-dimethyl-7-oxabicyclo[2.2.1]hept-5-en-1-yl derivatives can be converted with high stereoselectivity into polypropionate fragments such as (-)-(2R,3R,4R,5S)-5-(benzyloxy)-3-(isopropyloxy)-2,4-dimethylhept-6-enal ((-)-16) or (-)-(2R,2'S,3'S,4'S,5'S)-2-[4-(benzyloxy)tetrahydro-3,5-dimethyl-5-methoxyfur-2-yl]propanal ((-)-20). The latter underwent stereoselective cross-aldolization with the lithium enolate of (+)-(1S,4S,5S,6S)-6-exo-(benzyloxy)-1,5-endo-dimethyl-7-oxabicyclo[2.2.1]heptan-2-one ((+)-9) giving an aldol ((-)-23); like mode of aldolization) that can be converted into a polypropionate fragment containing nine contiguous stereogenic centers.