(2S,3R)-2-methyl-3-hydroxypentanoic acid | 77405-43-7

• 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,3R)-2-methyl-3-hydroxypentanoic acid
• 英文别名: (2S,3R)-3-hydroxy-2-methylpentanoic acid
• CAS: 77405-43-7
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: NVIHALDXJWGLFD-CRCLSJGQSA-N

物化性质

• 沸点：
  250.5±23.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-methyl-3-hydroxypentanoic acid 在 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 Pyr*CrO₃*HCl 、 sodium acetate 、 dipyridine chromium trioxide 、 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 、 二异丁基氢化铝 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 、 苯 为溶剂， 反应 66.83h， 生成 6-脱氧红霉内酯B
  参考文献：
  名称：

  Total synthesis of 6-deoxyerythronolide B

  摘要：

  DOI：

  10.1021/ja00396a051
• 作为产物：
  描述：

  <<3-(2S)-4R>-3-(2-Methyl-1,3-dioxo-pentyl)-4-(phenylmethyl)>-2-oxazolidinone 在 lithium hydroxide 、 zinc(II) tetrahydroborate 、 双氧水 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 生成 (2S,3R)-2-methyl-3-hydroxypentanoic acid
  参考文献：
  名称：

  Cane, David E.; Tan, Weitian; Ott, Walter R., Journal of the American Chemical Society, 1993, vol. 115, # 2, p. 527 - 535

  摘要：

  DOI：

文献信息

• Structural Elucidation of Twelve Novel Esters Composed of Five Fatty Acids and Three New Branched Alcohols Together with Four Monoterpenoids from Sancassania shanghaiensis (Acari: Acaridae)
  作者：Tomoyo SAKATA、Kimiko OKABE、Yasumasa KUWAHARA

  DOI：10.1271/bbb.65.919

  日期：2001.1

  A total of 12 novel esters and four monoterpenoids (rosefuran, (2R,3R)-epoxyneral, and α- and β-acaridials) were detected by GC/MS analyses as the opisthonotal gland components of Sancassania shanghaiensis. The acidic fraction after hydrolysis was composed of five common fatty acids (palmitic, stearic, oleic, linoleic and arachidic acid), while the alcoholic fraction consisted of two major components (C6 and C8 alcohols with branched methyls), together with a trace amount of C9 alcohol. The Two major alcohols were identified as new alcohols [(S)-2-methylpentanol and (2S,4S)-2,4-dimethylhexanol] by comparing the physico-chemical data of their 3,5-dinitrobenzoates with those of regio-selectively synthesized alcohols. The C9 alcohol was suggested as (2S,4S)-2,4-dimethylheptanol, based on a structural and biogenetic analogy to the C6 and C8 alcohols. Five of the compounds were each identified by GC to be (S)-2-methylpentyl esters from five fatty acids, and the other five components likewise as (2S,4S)-2,4-dimethylhexyl esters. The remaining two were suggested as (2S,4S)-2,4-dimethylheptyl Stearate and linolate.

  GC/MS分析在Sancassania shanghaiensis的抱粉腺成分中检测到总共12种新型酯和4种单萜（玫瑰呋喃、（2R,3R）-环氧橙花醇以及α-和β-刺檗二醇）。经过水解后的酸性部分由5种常见脂肪酸（棕榈酸、硬脂酸、油酸、亚油酸和花生酸）组成，而醇性部分则主要由两种成分（带有支链甲基的C6和C8醇）组成，同时含有微量的C9醇。通过比较其3,5-二硝基苯甲酸酯的物理化学数据与选择性合成醇的数据，确认这两种主要醇为新型醇[（S）-2-甲基戊醇和（2S,4S）-2,4-二甲基己醇]。根据结构和生物学上的相似性，C9醇被推测为（2S,4S）-2,4-二甲基庚醇。通过GC鉴定，五种化合物分别为五种脂肪酸的（S）-2-甲基戊酯，另外五种成分同样为（2S,4S）-2,4-二甲基己酯。剩下的两种被推测为（2S,4S）-2,4-二甲基庚酯的硬脂酸酯和亚油酸酯。
• Chiral propionate enolate equivalents for the stereoselective synthesis of threo- or erytho-α,-methyl-β-hydroxy acids
  作者：Stephen G. Davies、Isabelle M. Dordor-Hedgecock、Peter Warner

  DOI：10.1016/s0040-4039(00)94797-x

  日期：——

  derived from (η5-C5H5)Fe(CO)(PPh3)COCH2CH3 are chiral propionate enolate equivalents which on reaction with aldehydes (RCHO, RMe.Et,iPr,tBu) provide stereoselective syntheses of threo- and erytho-α-methyl-β-hydroxy acids respectively.

  从（η得到的铝和铜烯醇化物5 -C 5 H ^ 5）的Fe（CO）（PPH 3）COCH 2 CH 3是手性烯醇化物丙酸酯当量，将其用醛反应（RCHO，RMe.Et，我PR，（t Bu）分别提供苏-和异-α-甲基-β-羟基酸的立体选择性合成。
• The Thioesterase of the Erythromycin-Producing Polyketide Synthase: Influence of Acyl Chain Structure on the Mode of Release of Substrate Analogues from the Acyl Enzyme Intermediates
  作者：Kira J. Weissman、Cameron J. Smith、Ulf Hanefeld、Ranjana Aggarwal、Matthew Bycroft、James Staunton、Peter F. Leadlay

  DOI：10.1002/(sici)1521-3773(19980605)37:10<1437::aid-anie1437>3.0.co;2-7

  日期：1998.6.5

  synthase (PKS) have demonstrated that the ability of this enzyme to act as a universal decoupler is limited, but stereochemical variation is readily tolerated. Synthetic analogues with all four stereochemical configurations of the natural substrate's 2-methyl-3-hydroxy substitution pattern (1-4; X=p-nitrophenoxy) were substrates for the enzyme.

  基因工程化的聚酮化合物的生产主要取决于硫酯酶的活性以释放产品。用来自红霉素聚酮化合物合酶（PKS）的硫酯酶进行的体外研究表明，该酶用作通用解偶联剂的能力有限，但很容易耐受立体化学变异。具有天然底物的2-甲基-3-羟基取代模式（1-4； X =对硝基苯氧基）的所有四个立体化学构型的合成类似物是该酶的底物。
• Chiral acetate enolate equivalent for the synthesis of β-hydroxy acids
  作者：Stephen G. Davies、Isabelle M. Dordor、Peter Warner

  DOI：10.1039/c39840000956

  日期：——

  The aluminium enolate derived from (η5-C5H5)Fe(CO)(PPh3)(COMe) undergoes stereoselective aldol condensations with aldehydes to generate β-hydroxy acyl complexes which yield β-hydroxy acids on decomplexation.

  衍生自铝烯醇化物（η 5 -C 5 H ^ 5）的Fe（CO）（PPH 3）（COME）经历与醛立体选择性醛醇缩合，以生成β-羟基酰基络合物产率上解络β羟基酸。
• The thioesterase domain from the pimaricin and erythromycin biosynthetic pathways can catalyze hydrolysis of simple thioester substrates
  作者：Krishna K. Sharma、Christopher N. Boddy

  DOI：10.1016/j.bmcl.2007.03.060

  日期：2007.6

  biosynthetic pathways catalyze hydrolysis of a number of simple N-acetylcysteamine thioester derivatives. This study demonstrates that thioesterases are not highly substrate selective in formation of the acyl-enzyme intermediate, in contrast to non-ribosomal peptide synthase thioesterase domains that show very high specificity for substrate loading. This observation has important implications for the

  来自pimaricin和6-deoxyerythronolide B生物合成途径的重组聚酮化合物合酶硫酯酶结构域催化许多简单的N-乙酰半胱胺硫酯衍生物的水解。这项研究表明，与非核糖体肽合酶硫酯酶结构域对底物负载具有很高的特异性相比，硫酯酶在酰基酶中间体的形成中对底物的选择性不是很高。该观察结果对生产聚酮化合物产品的生物合成途径的工程设计具有重要意义。