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 | 952101-35-8

• 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: 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
• 英文别名: (1S,5S,6R,7S)-5-(methoxymethoxymethyl)-8,8-dimethyl-7-(4-methylphenoxy)carbothioyloxy-2-oxabicyclo[4.2.0]octan-3-one
• CAS: 952101-35-8
• 化学式: C₂₀H₂₆O₆S
• 分子量: 394.489
• InChiKey: FNPXUEYOBLXKQA-ZSGPHXLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  95.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  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 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.0h， 以61%的产率得到(1S,5S,6R)-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
• 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 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 氢气 、 四丁基碘化铵 、 臭氧 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、3.45 MPa 条件下， 反应 88.25h， 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

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).