3-methoxy-2-(4-methoxybenzyloxy)-5-methylhex-5-enoic acid | 866454-48-0

• 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: 3-methoxy-2-(4-methoxybenzyloxy)-5-methylhex-5-enoic acid
• 英文别名: (2S,3R)-3-methoxy-2-[(4-methoxyphenyl)methoxy]-5-methylhex-5-enoic acid
• CAS: 866454-48-0
• 化学式: C₁₆H₂₂O₅
• 分子量: 294.348
• InChiKey: TXJOALBXZZIKIQ-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-methoxy-2-(4-methoxybenzyloxy)-5-methylhex-5-enoic acid 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-methoxy-2-(4-methoxybenzyloxy)-5-methylhex-5-enoic acid methyl ester
  参考文献：
  名称：

  Stereochemical Assignment of the C₁−C₆ Fragment of Psymberin by Synthesis and Natural Product Degradation

  摘要：

  Psymberin is a sponge-derived natural product that shows striking selectivity as a cytotoxic agent. Conformational mobility has precluded stereochemical assignment for the acyl fragment of this molecule (psymberic acid) by NMR. Herein we report stereoselective syntheses of all four stereoisomers of psymberic acid. A comparison of the acid-mediated cyclization products of these compounds to the product of psymberin's acidic methanolysis showed the stereochemical configuration of this fragment to be 4S, 5S.

  DOI：

  10.1021/ol051396s
• 作为产物：
  描述：

  3-methoxy-2-(4-methoxybenzyloxy)-5-methylhex-5-enal 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 叔丁醇 为溶剂， 反应 0.5h， 生成 3-methoxy-2-(4-methoxybenzyloxy)-5-methylhex-5-enoic acid
  参考文献：
  名称：

  Stereochemical Assignment of the C₁−C₆ Fragment of Psymberin by Synthesis and Natural Product Degradation

  摘要：

  Psymberin is a sponge-derived natural product that shows striking selectivity as a cytotoxic agent. Conformational mobility has precluded stereochemical assignment for the acyl fragment of this molecule (psymberic acid) by NMR. Herein we report stereoselective syntheses of all four stereoisomers of psymberic acid. A comparison of the acid-mediated cyclization products of these compounds to the product of psymberin's acidic methanolysis showed the stereochemical configuration of this fragment to be 4S, 5S.

  DOI：

  10.1021/ol051396s

文献信息

• Studies toward the Unique Pederin Family Member Psymberin: Full Structure Elucidation, Two Alternative Total Syntheses, and Analogs
  作者：Yu Feng、Xin Jiang、Jef K. De Brabander

  DOI：10.1021/ja3057612

  日期：2012.10.17

  Two synthetic approaches to psymberin have been accomplished. A highly convergent first generation synthesis led to the complete stereochemical assignment and demonstrated that psymberin and irciniastatin A are identical compounds. This synthesis featured a diastereoselective aldol coupling between the aryl fragment and a central tetrahydropyran core and a novel one-pot procedure to convert an amide, via intermediacy of a sensitive methyl imidate, to the N-acyl aminal reminiscent of psymberin. The highlights of the second generation synthesis include an efficient iridium-catalyzed enantioselective bisallylation of neopentyl glycol and a stepwise Sonogashira coupling/cycloisomerization/reduction sequence to construct the dihydroisocoumarin unit. The two synthetic avenues were achieved in 17-18 steps (longest linear sequence, similar to 14-15 isolations) from 3 fragments prepared in 7-8 (first generation) and 3-8 (second generation) steps each. This convergent approach allowed for the preparation of sufficient amounts of psymberin (similar to 0.5 g) for follow-up biological studies. Meanwhile, our highly flexible strategy enabled the design and synthesis of multiple analogs, including a psymberin pederin hybrid, termed psympederin, that proved crucial to a comprehensive understanding of the chemical biology of psymberin and related compounds that will be described in a subsequent manuscript.
• Stereochemical Assignment of the C₁−C₆ Fragment of Psymberin by Synthesis and Natural Product Degradation
  作者：Michael E. Green、Jason C. Rech、Paul E. Floreancig

  DOI：10.1021/ol051396s

  日期：2005.9.1

  Psymberin is a sponge-derived natural product that shows striking selectivity as a cytotoxic agent. Conformational mobility has precluded stereochemical assignment for the acyl fragment of this molecule (psymberic acid) by NMR. Herein we report stereoselective syntheses of all four stereoisomers of psymberic acid. A comparison of the acid-mediated cyclization products of these compounds to the product of psymberin's acidic methanolysis showed the stereochemical configuration of this fragment to be 4S, 5S.