(3S,4S,2'S)-3-hexyl-4-(2'-benzyloxyhept-1'-yl)oxetan-2-one | 907217-55-4

• 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: (3S,4S,2'S)-3-hexyl-4-(2'-benzyloxyhept-1'-yl)oxetan-2-one
• 英文别名: (3S,4S)-3-hexyl-4-[(2S)-2-phenylmethoxyheptyl]oxetan-2-one
• CAS: 907217-55-4
• 化学式: C₂₃H₃₆O₃
• 分子量: 360.537
• InChiKey: HOYIRUCGYONWKC-FKBYEOEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S,2'S)-3-hexyl-4-(2'-benzyloxyhept-1'-yl)oxetan-2-one 在 Pd/C 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以96%的产率得到(3S,4S,2'S)-3-hexyl-4-(2'-hydroxyhept-1'-yl)oxetan-2-one
  参考文献：
  名称：

  Asymmetric synthesis of tetrahydrolipstatin and valilactone

  摘要：

  The highly diastereoselective aldol reaction between acyl complexes of the iron chiral auxiliary [(eta(5)-C5H5)Fe(CO)(PPh3)] and beta-hydroxy aldehydes (obtained via a Noyori asymmetric hydrogenation), followed by a tandem oxidative decomplexation-cyclisation process gives access to beta-substituted and alpha,beta-disubstituted beta-lactones in high ee. This methodology has been employed in the asymmetric syntheses of tetra hydrolipstatin and valilactone. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.012
• 作为产物：
  描述：

  (S)-carbonyl(cyclopentadienyl)octanoyl(triphenylphosphino)iron 、 (S)-3-benzyloxyoctanal 在 正丁基锂 、 氯化二乙基铝 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以130 mg的产率得到(3S,4S,2'S)-3-hexyl-4-(2'-benzyloxyhept-1'-yl)oxetan-2-one
  参考文献：
  名称：

  Asymmetric synthesis of tetrahydrolipstatin and valilactone

  摘要：

  The highly diastereoselective aldol reaction between acyl complexes of the iron chiral auxiliary [(eta(5)-C5H5)Fe(CO)(PPh3)] and beta-hydroxy aldehydes (obtained via a Noyori asymmetric hydrogenation), followed by a tandem oxidative decomplexation-cyclisation process gives access to beta-substituted and alpha,beta-disubstituted beta-lactones in high ee. This methodology has been employed in the asymmetric syntheses of tetra hydrolipstatin and valilactone. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.012

文献信息

• An Expeditious Enantioselective Total Synthesis of Valilactone
  作者：Yikang Wu、Ya-Ping Sun

  DOI：10.1021/jo060844m

  日期：2006.7.1

  The title compound was synthesized through an expeditious route using Crimmins aldolization to establish the two key stereogenic centers and a hydroxyl group activation (HGA) protocol to construct the anti alpha,beta-disubstituted beta-lactone from the corresponding syn aldol.
• US5245056A
  申请人：——

  公开号：US5245056A

  公开（公告）日：1993-09-14
• US5399720A
  申请人：——

  公开号：US5399720A

  公开（公告）日：1995-03-21
• Asymmetric synthesis of tetrahydrolipstatin and valilactone
  作者：Stephen C. Case-Green、Stephen G. Davies、Paul M. Roberts、Angela J. Russell、James E. Thomson

  DOI：10.1016/j.tetasy.2008.11.012

  日期：2008.11

  The highly diastereoselective aldol reaction between acyl complexes of the iron chiral auxiliary [(eta(5)-C5H5)Fe(CO)(PPh3)] and beta-hydroxy aldehydes (obtained via a Noyori asymmetric hydrogenation), followed by a tandem oxidative decomplexation-cyclisation process gives access to beta-substituted and alpha,beta-disubstituted beta-lactones in high ee. This methodology has been employed in the asymmetric syntheses of tetra hydrolipstatin and valilactone. (C) 2008 Elsevier Ltd. All rights reserved.