methyl (1S,2S,3R)-2-[3-hydroxy-2-(hydroxymethyl)prop-1-enyl]-6-oxo-3-propan-2-ylcyclohexane-1-carboxylate | 179331-61-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl (1S,2S,3R)-2-[3-hydroxy-2-(hydroxymethyl)prop-1-enyl]-6-oxo-3-propan-2-ylcyclohexane-1-carboxylate
• CAS: 179331-61-4
• 化学式: C₁₅H₂₄O₅
• 分子量: 284.353
• InChiKey: KLTGELVXFDEUHS-BZPMIXESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 methyl (1S,2S,3R)-2-[3-hydroxy-2-(hydroxymethyl)prop-1-enyl]-6-oxo-3-propan-2-ylcyclohexane-1-carboxylate 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到(1S,2S,3R)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-propenyl]-3-isopropyl-6-oxo-cyclohexanecarboxylic acid methyl ester
  参考文献：
  名称：

  EPC合成（+）-庚二酸的关键一步

  摘要：

  通过X射线结构分析确定了烯醇酸酯3n和4n的绝对构型，它们被制备为EPC合成抗生素（+）-庚二酸的手性结构单元。将缩醛保护的乙烯基铜酸酯共轭添加到5'R构型的烯酸酯3n中，以79％的收率得到作为单一非对映异构体的加合物9n。此外，还研究了从9n上裂解辅助基和缩醛保护基的方法。最后，我们获得了对映体纯形式的甲硅烷基保护的β-酮酸酯13，其是合成庚二酸的已知中间体。

  DOI：

  10.1016/0040-4020(96)00428-0
• 作为产物：
  描述：

  (1S,2S)-2-(2,2-Dimethyl-[1,3]dioxan-5-ylidenemethyl)-3-isopropyl-6-oxo-cyclohexanecarboxylic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 26.0h， 生成 methyl (1S,2S,3R)-2-[3-hydroxy-2-(hydroxymethyl)prop-1-enyl]-6-oxo-3-propan-2-ylcyclohexane-1-carboxylate
  参考文献：
  名称：

  EPC synthesis of (+)-heptelidic acid

  摘要：

  An EPC (enantiomerically pure compound) synthesis of the antibiotic natural product (+)-heptelidic acid (1) is presented. Key step of the synthesis is a conjugate addition of the acetal protected vinyl cuprate 4 to the auxiliary shielded enoate 5n which gives the adduct 7n as a single diastereomer. After cleavage of the acetal protecting group and of the chiral auxiliary the enantiomerically pure beta-ketoester 12 has been obtained which has been transformed to the title compound 1 (11 steps starting from 5n, 10.6% overall yield).

  DOI：

  10.1007/bf00807894

文献信息

• A key step towards EPC synthesis of (+)-heptelidic acid
  作者：Gerhard Riehs、Ernst Urban、Horst Völlenkle

  DOI：10.1016/0040-4020(96)00428-0

  日期：1996.6

  blocks for the EPC synthesis of the antibiotic (+)-heptelidic acid, was determined by X-ray structure analysis. Conjugate addition of an acetal protected vinylcuprate to the 5′R configurated enoate 3n gave adduct 9n as a single diastereomer in 79% yield. Further, cleavage of the auxiliary and of the acetal protecting group from 9n were studied. Finally, we obtained the silyl protected β-ketoester 13

  通过X射线结构分析确定了烯醇酸酯3n和4n的绝对构型，它们被制备为EPC合成抗生素（+）-庚二酸的手性结构单元。将缩醛保护的乙烯基铜酸酯共轭添加到5'R构型的烯酸酯3n中，以79％的收率得到作为单一非对映异构体的加合物9n。此外，还研究了从9n上裂解辅助基和缩醛保护基的方法。最后，我们获得了对映体纯形式的甲硅烷基保护的β-酮酸酯13，其是合成庚二酸的已知中间体。
• EPC synthesis of (+)-heptelidic acid
  作者：G. Riehs、E. Urban

  DOI：10.1007/bf00807894

  日期：1997.3

  An EPC (enantiomerically pure compound) synthesis of the antibiotic natural product (+)-heptelidic acid (1) is presented. Key step of the synthesis is a conjugate addition of the acetal protected vinyl cuprate 4 to the auxiliary shielded enoate 5n which gives the adduct 7n as a single diastereomer. After cleavage of the acetal protecting group and of the chiral auxiliary the enantiomerically pure beta-ketoester 12 has been obtained which has been transformed to the title compound 1 (11 steps starting from 5n, 10.6% overall yield).