methyl (R)-3-hydroxy-12-methyltridecanoate | 159690-67-2

• 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: methyl (R)-3-hydroxy-12-methyltridecanoate
• 英文别名: methyl (3R)-3-hydroxy-12-methyltridecanoate
• CAS: 159690-67-2
• 化学式: C₁₅H₃₀O₃
• 分子量: 258.401
• InChiKey: CTKJHQJNISBVHK-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 methyl (R)-3-hydroxy-12-methyltridecanoate 在 吡啶 作用下， 生成 (R)-12-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-tridecanoic acid methyl ester
  参考文献：
  名称：

  Application of microbial enantiofacially selective hydrolysis in natural product synthesis

  摘要：

  Pichinia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70% yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87%e.e.), to be the starting material for the synthesis of optically active natural products. Methyl (R)3-hydroxy-12- methyltridecanoate. a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation. Final products were enantiomerically enriched to 94-95% e.e., by the lipase-mediated enantioselective transesterification which could remove the minor enantiomer as the corresponding acetate.

  DOI：

  10.1016/s0957-4166(00)86269-2
• 作为产物：
  描述：

  methyl (6R)-6-tetrahydropyranyloxy-7-phenylheptanoate 在 palladium on activated charcoal 吡啶 、 ruthenium trichloride 、 sodium hydroxide 、 sodium periodate 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 氢气 、 4-甲基苯磺酸吡啶 、 lithium 作用下， 以 四氯化碳 、 乙醚 、 乙醇 、 乙腈 为溶剂， 反应 21.0h， 生成 methyl (R)-3-hydroxy-12-methyltridecanoate
  参考文献：
  名称：

  Application of microbial enantiofacially selective hydrolysis in natural product synthesis

  摘要：

  Pichinia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70% yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87%e.e.), to be the starting material for the synthesis of optically active natural products. Methyl (R)3-hydroxy-12- methyltridecanoate. a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation. Final products were enantiomerically enriched to 94-95% e.e., by the lipase-mediated enantioselective transesterification which could remove the minor enantiomer as the corresponding acetate.

  DOI：

  10.1016/s0957-4166(00)86269-2

文献信息

• Application of microbial enantiofacially selective hydrolysis in natural product synthesis
  作者：Osamu Katoh、Takeshi Sugai、Hiromichi Ohta

  DOI：10.1016/s0957-4166(00)86269-2

  日期：1994.10

  Pichinia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70% yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87%e.e.), to be the starting material for the synthesis of optically active natural products. Methyl (R)3-hydroxy-12- methyltridecanoate. a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation. Final products were enantiomerically enriched to 94-95% e.e., by the lipase-mediated enantioselective transesterification which could remove the minor enantiomer as the corresponding acetate.