(R,R)-methyl psymberate | 866454-66-2

• 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: (R,R)-methyl psymberate
• 英文别名: 2-hydroxy-3-methoxy-5-methylhex-5-enoic acid methyl ester；(2R,3R)-methyl 2-hydroxy-3-methoxy-5-methylhex-5-enoate
• CAS: 866454-66-2
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: OHHIDMQUORCCBD-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R,R)-methyl psymberate 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 (2R,3R)-3-methoxy-5,5-dimethyltetrahydrofuran-2-carboxylic 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 、 氯化亚砜 、 2-甲基-2-丁烯 、 ammonium cerium(IV) nitrate 、 水 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 、 叔丁醇 为溶剂， 反应 1.5h， 生成 (R,R)-methyl psymberate
  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