(2S,4S)-2,4-dimethyloctanoic acid | 177607-85-1

• 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: (2S,4S)-2,4-dimethyloctanoic acid
• CAS: 177607-85-1
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: BBRLCIVWEAHSPK-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Acetic acid (1R,2S)-2-({(S)-1-[(2S,4S)-4-hydroxy-2-((S)-2-methyl-5-oxo-2,5-dihydro-pyrrole-1-carbonyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-methyl-carbamoyl)-1-methyl-2-((S)-4-methyl-2-methylamino-pentanoylamino)-ethyl ester; hydrochloride 、 (2S,4S)-2,4-dimethyloctanoic acid 在 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 [(2R,3S)-3-[[(2S)-2-[[(2S,4S)-2,4-dimethyloctanoyl]-methylamino]-4-methylpentanoyl]amino]-4-[[(2S)-1-[(2S,4S)-4-hydroxy-2-[(2S)-2-methyl-5-oxo-2H-pyrrole-1-carbonyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-methylamino]-4-oxobutan-2-yl] acetate
  参考文献：
  名称：

  Total Asymmetric Synthesis of the Potent Immunosuppressive Marine Natural Product Microcolin A

  摘要：

  The total asymmetric synthesis of the potent immunosuppressive compound microcolin A is reported, The synthesis establishes the absolute stereochemistry of microcolin A as C-36R, C-38R, and C-4S on the basis of the diastereoselective preparation of all four possible diastereomers of the lipid region (fragment A) and diastereoselective synthesis of fragment C starting from natural L-(S)-alanine. The strategy involves a convergent assemblage of three optically pure fragments and is amenable to chemical modifications to examine structural analogs for biological study.

  DOI：

  10.1021/jo952123l
• 作为产物：
  描述：

  (3(2S,4S)4R)-3-(2,4-dimethyloctanoyl)-4-benzyl-2-oxazolidinone 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 以93%的产率得到(2S,4S)-2,4-dimethyloctanoic acid
  参考文献：
  名称：

  Total Asymmetric Synthesis of the Potent Immunosuppressive Marine Natural Product Microcolin A

  摘要：

  The total asymmetric synthesis of the potent immunosuppressive compound microcolin A is reported, The synthesis establishes the absolute stereochemistry of microcolin A as C-36R, C-38R, and C-4S on the basis of the diastereoselective preparation of all four possible diastereomers of the lipid region (fragment A) and diastereoselective synthesis of fragment C starting from natural L-(S)-alanine. The strategy involves a convergent assemblage of three optically pure fragments and is amenable to chemical modifications to examine structural analogs for biological study.

  DOI：

  10.1021/jo952123l

文献信息

• Synthesis of <scp>Anti‐Pancreatic</scp> Cancer Natural Product Majusculamide D and Analogues Reveals a Preliminary <scp>Structure‐Activity</scp> Relationships
  作者：Xiuhe Zhao、Mengxue Lv、Xiaonan Xi、Yaxin Lu、Liang Wang、Yue Chen

  DOI：10.1002/cjoc.202300526

  日期：2024.3.15

  The total synthesis of majusculamide D (1) was achieved from commercially available materials. In addition, we synthesized eight analogues including three stereoisomers of majusculamide D that differ in the fatty acid chain. Six analogues including a simplified analogue 29 exhibited significant nanomolar-level IC50 values against Panc-1 cells in MTT assays. A preliminary SAR analysis indicated that

  majusculamide D ( 1 )的全合成是由市售材料实现的。此外，我们还合成了八种类似物，包括三种脂肪酸链不同的 majusculamide D 立体异构体。在 MTT 测定中，包括简化类似物29在内的六种类似物对 Panc-1 细胞表现出显着的纳摩尔水平 IC 50值。初步的SAR分析表明majusculamide D的C 10 和C 2− C 3 不饱和双键上的羟基对于维持对Panc-1细胞的高活性以及C 40-Me 和C 42-Me基团的定向至关重要是可以忍受的。
• Sex Pheromone of the Pine Sawfly, Macrodiprion nemoralis. Stereoselective Synthesis of the Sixteen Stereoisomers of 3,7,9-Trimethyl-2-tridecyl Acetate.
  作者：Staffan Karlsson、Erik Hedenström、Luis Lezama、María I. Arriortua、Margareta Björkman、Benita H. Forngren、Tobias Forngren、Per Hartvig、Karin Markides、Ulrika Yngve、Mattias Ögren

  DOI：10.3891/acta.chem.scand.53-0620

  日期：——

  The sixteen stereoisomers of 3,7,9-trimethyl-2-tridecyl acetate (5Ac) were prepared individually, each in over 99.5% stereochemical purity. The syntheses were based on the ring opening of a pure enantiomer of cis-3,4-dimethyl-gamma-butyrolactone using a pure stereoisomer of 1-lithio-2,4-dimethyloctane, the two stereogenic centres of which were introduced with high selectivity by alkylations of the amide enolates from the appropriate enantiomers of pseudoephedrine. (2S,3R,7R,9S)-3,7,9-Trimethyl-2-tridecyl acetate (SRRS-5Ac) has recently been found to be the major component of the female sex pheromone of Macrodiprion nemoralis (Hymenoptera: Diprionidae). A synthetic method for the preparation of a sixteen isomer mixture of 5Ac is also presented. This mixture has been found to be biologically active in field tests.
• Total Asymmetric Synthesis of the Potent Immunosuppressive Marine Natural Product Microcolin A
  作者：Carl P. Decicco、Paul Grover

  DOI：10.1021/jo952123l

  日期：1996.1.1

  The total asymmetric synthesis of the potent immunosuppressive compound microcolin A is reported, The synthesis establishes the absolute stereochemistry of microcolin A as C-36R, C-38R, and C-4S on the basis of the diastereoselective preparation of all four possible diastereomers of the lipid region (fragment A) and diastereoselective synthesis of fragment C starting from natural L-(S)-alanine. The strategy involves a convergent assemblage of three optically pure fragments and is amenable to chemical modifications to examine structural analogs for biological study.