Methyl (2E,5S,7R)-7-benzyloxy-5-hydroxy-2,9-decanedienoate | 201419-21-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Methyl (2E,5S,7R)-7-benzyloxy-5-hydroxy-2,9-decanedienoate
• 英文别名: methyl (2E,5S,7R)-5-hydroxy-7-phenylmethoxydeca-2,9-dienoate
• CAS: 201419-21-8
• 化学式: C₁₈H₂₄O₄
• 分子量: 304.386
• InChiKey: VLUZCRQZNYKTSH-SVWBTXMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl (2E,5S,7R)-7-benzyloxy-5-hydroxy-2,9-decanedienoate 在 potassium tert-butylate 、 水 、 palladium dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.25h， 生成 (2R,2''S,4R,6R)-6-(2''-Benzyloxy-4''-oxopentenyl)-4-(methoxycarbonylmethyl)-2-phenyl-1,3-dioxane
  参考文献：
  名称：

  General and Asymmetric Synthesis of Protected 1,3,5-Triols with Pendant Functional Groups

  摘要：

  A stereoselective synthesis of enantiomerically purl 1,3,5-triols of any configuration has been developed. These triols carry suitable functional groups at the termini of the chain which should allow for easy and efficient coupling of two building blocks. The silyloxy-Cope rearrangement of syn-aldols was used to prepare a common advanced intermediate for the synthesis of all four stereoisomeric triols. Three synthetic operations-an allylboration, an oxidative desilylation, and a conjugate addition reaction-were employed to assemble the target molecules. Their terminal double bond may either be cleaved to give the corresponding aldehydes or oxidized to the methyl ketones in a Wacker process to provide access to two subunits for a coupling reaction.

  DOI：

  10.1002/(sici)1521-3765(19991001)5:10<2850::aid-chem2850>3.0.co;2-7
• 作为产物：
  描述：

  (E,3S)-7-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-[dimethyl(phenyl)silyl]-7-oxohept-5-enal 在 potassium fluoride 、 三氟甲磺酸 、 MeOMgCl 、 双氧水 、 boron trifluoride diacetate 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 10.08h， 生成 Methyl (2E,5S,7R)-7-benzyloxy-5-hydroxy-2,9-decanedienoate
  参考文献：
  名称：

  通过手性醛醇缩合产物的应对重排合成对映选择性多元醇。制霉菌素A 1的C 1 -C 10片段的合成

  摘要：

  描述了完全抑制的制霉菌素A 1的C 1 -C 10-多元醇片段的立体选择性合成。手性醛醇缩合产物1的氧-Cope重排提供了作为关键中间体的醛3，其通过对映选择性的烯丙基硼化和半缩醛-醇盐的分子内共轭添加而转化为天然产物片段。©1997 Elsevier ScienceLtd。保留所有权利。

  DOI：

  10.1016/s0040-4039(97)10455-5

文献信息

• General and Asymmetric Synthesis of Protected 1,3,5-Triols with Pendant Functional Groups
  作者：Christoph Schneider、Markus Rehfeuter

  DOI：10.1002/(sici)1521-3765(19991001)5:10<2850::aid-chem2850>3.0.co;2-7

  日期：1999.10.1

  A stereoselective synthesis of enantiomerically purl 1,3,5-triols of any configuration has been developed. These triols carry suitable functional groups at the termini of the chain which should allow for easy and efficient coupling of two building blocks. The silyloxy-Cope rearrangement of syn-aldols was used to prepare a common advanced intermediate for the synthesis of all four stereoisomeric triols. Three synthetic operations-an allylboration, an oxidative desilylation, and a conjugate addition reaction-were employed to assemble the target molecules. Their terminal double bond may either be cleaved to give the corresponding aldehydes or oxidized to the methyl ketones in a Wacker process to provide access to two subunits for a coupling reaction.
• Enantioselective Polyol Synthesis via the Cope Rearrangement of Chiral Aldol Products. A Synthesis of the C1-C10-Fragment of Nystatin A1
  作者：Christoph Schneider、Markus Rehfeuter

  DOI：10.1016/s0040-4039(97)10455-5

  日期：1998.1

  A stereoselective synthesis of a fully protected C1-C10-polyol-fragment of nystatin A1 is described. The oxy-Cope rearrangement of the chiral aldol product 1 affords the aldehyde 3 as the key intermediate which is converted into the natural product fragment by enantioselective allylboration and intramolecular conjugate addition of a hemiacetal-alkoxide. © 1997 Elsevier Science Ltd. All rights reserved

  描述了完全抑制的制霉菌素A 1的C 1 -C 10-多元醇片段的立体选择性合成。手性醛醇缩合产物1的氧-Cope重排提供了作为关键中间体的醛3，其通过对映选择性的烯丙基硼化和半缩醛-醇盐的分子内共轭添加而转化为天然产物片段。©1997 Elsevier ScienceLtd。保留所有权利。