3-methoxy-2-(4-methoxybenzyloxy)-5-methylhex-5-enoic acid methyl ester | 866454-61-7

• 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 methyl ester
• 英文别名: (2S,3S)-methyl 3-methoxy-2-(4-methoxybenzyloxy)-5-methylhex-5-enoate；methyl (2S,3S)-3-methoxy-2-[(4-methoxyphenyl)methoxy]-5-methylhex-5-enoate
• CAS: 866454-61-7
• 化学式: C₁₇H₂₄O₅
• 分子量: 308.375
• InChiKey: UJVBZEAZQUFLOD-HOTGVXAUSA-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：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  3-methoxy-2-(4-methoxybenzyloxy)-5-methylhex-5-enoic acid methyl ester 在 ammonium cerium(IV) nitrate 、 水 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以60%的产率得到2-hydroxy-3-methoxy-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-en-1-ol 在 sodium chlorite 、 sodium dihydrogenphosphate 、 氯化亚砜 、 2-甲基-2-丁烯 、 pyridine-SO3 complex 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 2.83h， 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

文献信息

• Chemoenzymatic Synthesis of (Protected) Psymberic Acid
  作者：Jörg Pietruszka、Robert Christian Simon

  DOI：10.1002/ejoc.200900292

  日期：2009.7

  Two alternative approaches to the side-chain of psymberin (1), psymberic acid (5), have been developed starting from either racemic or enantiopure acetal 6. A five-step chemoenzymatic route provided the PMB-protected acid (S,S)-16 required for the coupling that should ultimately lead to the natural product 1. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  已经从外消旋或对映纯缩醛 6 开始开发了 psymberin (1) 侧链的两种替代方法 psymberic acid (5)。五步化学酶促路线提供了 PMB 保护的酸 (S,S)-最终产生天然产物 1 的偶联所需的 16。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009）