(1S,5S,6S,7S)-7-benzyloxy-5-(methoxymethoxymethyl)-8,8-dimethyl-2-oxabicyclo[4.2.0]octan-3-one | 952092-36-3

• 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: (1S,5S,6S,7S)-7-benzyloxy-5-(methoxymethoxymethyl)-8,8-dimethyl-2-oxabicyclo[4.2.0]octan-3-one
• 英文别名: (1S,5S,6S,7S)-5-(methoxymethoxymethyl)-8,8-dimethyl-7-phenylmethoxy-2-oxabicyclo[4.2.0]octan-3-one
• CAS: 952092-36-3
• 化学式: C₁₉H₂₆O₅
• 分子量: 334.412
• InChiKey: JLBTYNMCJYEWQT-UBDQQSCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,5S,6S,7S)-7-benzyloxy-5-(methoxymethoxymethyl)-8,8-dimethyl-2-oxabicyclo[4.2.0]octan-3-one 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 thiocarbonic acid [(1S,5S,6S,7S)-7-hydroxy-5-(methoxymethoxymethyl)-8,8-dimethyl-3-oxo-2-oxabicyclo[4.2.0]oct-7-yl] ester p-tolyl ester
  参考文献：
  名称：

  Pestalotiopsin A. Enantioselective Construction of Potential Building Blocks Derived from Antipodal Cyclobutanol Intermediates

  摘要：

  [GRAPHICS]D-Glyceraldehyde acetonide has been used as the starting point for accessing the enantiomeric cyclobutanols 11 in optically pure condition. The dextrorotatory enantiomer has been transformed in five steps into the [3.2.0] bicyclic lactone 22. While the deoxygenation of 22 proved to be problematical, the uncyclized variant 25 underwent the Barton process smoothly. These findings guided the related conversion of (-)-11 into 34. Use was also made of ring-closing metathesis to bring about the conversion of (+)-11 into [4.2.0] bicyclic lactone building blocks. In general, all three pathways are efficient and offer the prospect of practical side-chain appendage for the purpose of installing the nine-membered ring of pestalotiopsin A (1).

  DOI：

  10.1021/jo070861r
• 作为产物：
  描述：

  (1S,5R,6S,7S)-7-benzyloxy-8,8-dimethyl-5-vinyl-2-oxabicyclo[4.2.0]octan-3-one 在 sodium tetrahydroborate 、 四丁基碘化铵 、 臭氧 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.25h， 生成 (1S,5S,6S,7S)-7-benzyloxy-5-(methoxymethoxymethyl)-8,8-dimethyl-2-oxabicyclo[4.2.0]octan-3-one
  参考文献：
  名称：

  Pestalotiopsin A. Enantioselective Construction of Potential Building Blocks Derived from Antipodal Cyclobutanol Intermediates

  摘要：

  [GRAPHICS]D-Glyceraldehyde acetonide has been used as the starting point for accessing the enantiomeric cyclobutanols 11 in optically pure condition. The dextrorotatory enantiomer has been transformed in five steps into the [3.2.0] bicyclic lactone 22. While the deoxygenation of 22 proved to be problematical, the uncyclized variant 25 underwent the Barton process smoothly. These findings guided the related conversion of (-)-11 into 34. Use was also made of ring-closing metathesis to bring about the conversion of (+)-11 into [4.2.0] bicyclic lactone building blocks. In general, all three pathways are efficient and offer the prospect of practical side-chain appendage for the purpose of installing the nine-membered ring of pestalotiopsin A (1).

  DOI：

  10.1021/jo070861r

文献信息

• Pestalotiopsin A. Enantioselective Construction of Potential Building Blocks Derived from Antipodal Cyclobutanol Intermediates
  作者：Leo A. Paquette、Gregory D. Parker、Takahiro Tei、Shuzhi Dong

  DOI：10.1021/jo070861r

  日期：2007.9.1

  [GRAPHICS]D-Glyceraldehyde acetonide has been used as the starting point for accessing the enantiomeric cyclobutanols 11 in optically pure condition. The dextrorotatory enantiomer has been transformed in five steps into the [3.2.0] bicyclic lactone 22. While the deoxygenation of 22 proved to be problematical, the uncyclized variant 25 underwent the Barton process smoothly. These findings guided the related conversion of (-)-11 into 34. Use was also made of ring-closing metathesis to bring about the conversion of (+)-11 into [4.2.0] bicyclic lactone building blocks. In general, all three pathways are efficient and offer the prospect of practical side-chain appendage for the purpose of installing the nine-membered ring of pestalotiopsin A (1).