methyl (2S)-2-hydroxy-3,3-dimethylbutanoate | 103499-39-4

• 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 (2S)-2-hydroxy-3,3-dimethylbutanoate
• 英文别名: (S)-methyl 2-hydroxy-3,3-dimethylbutanoate；(S)-methyl 3,3-dimethyl-2-hydroxybutanoate；methyl 2-hydroxy-3,3-dimethylbutanoate；methyl S-(+)-2-hydroxy-3,3-dimethylbutanoate
• CAS: 103499-39-4
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: YYAKMBGOMGURAY-RXMQYKEDSA-N

物化性质

• 沸点：
  161.8±8.0 °C(Predicted)
• 密度：
  1.004±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  methyl (2S)-2-hydroxy-3,3-dimethylbutanoate 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 乙醚 为溶剂， 反应 27.17h， 生成 (2S)-2-benzyloxy-3,3-dimethylbutanol
  参考文献：
  名称：

  Chiral Preparation of (R)- and (S)-3-(Benzyloxy)-4,4-dimethyl-1-pentene

  摘要：

  简便制备具有光学活性的烯丙基醚的方法已经开发出来，这种烯丙基醚在烯丙基手性中心带有叔丁基，即（R）和（S）两种对映形式的2-（苄氧基）-3,3-二甲基-1-戊烯。这些化合物预计将成为高效且高度立体选择性的极性亲二体，在不对称硝酮环加成反应中表现优异。该方法利用了商业上可获得的L-叔亮氨酸和（R）-泛醇酸内酯分别作为手性前体。

  DOI：

  10.1055/s-1993-25817
• 作为产物：
  描述：

  3,3-二甲基-2-氧代丁酸甲酯 在 potassium 9-O-(1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl)-9-boratabicyclo<3.3.1>nonane 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以85%的产率得到methyl (2S)-2-hydroxy-3,3-dimethylbutanoate
  参考文献：
  名称：

  Chiral synthesis via organoboranes. 15. Selective reductions. 42. Asymmetric reduction of representative prochiral ketones with potassium 9-O-(1,2:5,6-di-O-isopropylidene-.alpha.-D-glucofuranosyl)-9-boratabicyclo[3.3.1]nonane

  摘要：

  DOI：

  10.1021/jo00241a021

文献信息

• Camphor-based Schiff base ligand SBAIB: an enantioselective catalyst for addition of phenylacetylene to aldehydes
  作者：Ramalingam Boobalan、Chinpiao Chen、Gene-Hsian Lee

  DOI：10.1039/c1ob06683h

  日期：——

  series of Schiff base ligands were synthesized from (1R)-camphor. Under the optimal conditions, (+)-SBAIB-a, 10 was found to be an excellent catalyst for the enantioselective addition of phenylacetylene to various aldehydes without utilizing either achiral additives or Ti(OiPr)4. This approach yielded (R)-propargylic alcohols in extremely high yields (up to 99%) and excellent enantioselectivities (up to

  从中合成了一系列席夫碱配体 （1 R）-樟脑。在最佳条件下（+）-SBAIB-a，10被发现是用于对映选择性加成的极好的催化剂苯乙炔 无需使用非手性添加剂或 钛（O i Pr）4。该方法以极高的产率（高达99％）和优异的对映选择性（高达92％）产生了（R）-丙炔醇。相应的（S）-丙炔醇的合成具有良好的对映选择性（高达91％）和极好的收率（高达99％），使用（-）-SBAIB-a，41岁。
• [EN] HEPATITIS C INHIBITOR DIPEPTIDE ANALOGS<br/>[FR] ANALOGUES DIPEPTIDIQUES D'INHIBITEURS DE L'HEPATITE C
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2006007700A1

  公开（公告）日：2006-01-26

  The present invention relates to compounds of formula (I): wherein R1, R2, R4, n and m are as defined herein and R3 is selected from: (i) -C(O)OR31 wherein R31 is (C1-6)alkyl or aryl, wherein the (C1-6)alkyl is optionally substituted with one to three halogen substituents; (ii) -C(O)NR32R33, wherein R32 and R33 are each independently selected form H, (C1-6)alkyl, and Het; (iii) -SOvR34, wherein v is 1 or 2 and R34 is selected from: (C1-6)alkyl, aryl, Het, and NR32R33 wherein R32 and R33 are as defined above; and (iv) -CO(O)-R35, wherein R35 is selected from (C1-8)alkyl, (C3-7)cycloalkyl-(C1-4)alkyl, aryl, aryl-(C1-6)alkyl, Het and Het-(C1-6)alkyl, each of which are optionally substituted with one or more substituents each independently selected from halo, (C1-6)alkyl, (C3-7)cycloalkyl, aryl, Het, hydroxyl, -O-(C1-6)alkyl, -S-(C1-6)alkyl, -SO-(C1-6)alkyl, -SO2-(C1-6)alkyl, -O-aryl, -S-aryl, -SO-aryl and -SO2-aryl, wherein the aryl portion of the -O-aryl, -S-aryl, -SO-aryl and -SO2-aryl are each optionally substituted with one to five halo substituents. The present invention further relates to pharmaceutical compositions containing the compounds of formula (I) and methods for using these analogs in the treatment of HCV infection.

  本发明涉及以下式(I)的化合物：其中R1、R2、R4、n和m如本文所定义，R3选自：(i)-C(O)OR31，其中R31为(C1-6)烷基或芳基，其中(C1-6)烷基可选择地用一到三个卤素取代基取代；(ii)-C(O)NR32R33，其中R32和R33各自独立地选自H、(C1-6)烷基和Het；(iii)-SOvR34，其中v为1或2，R34选自：(C1-6)烷基、芳基、Het和NR32R33，其中R32和R33如上所定义；和(iv)-CO(O)-R35，其中R35选自(C1-8)烷基、(C3-7)环烷基-(C1-4)烷基、芳基、芳基-(C1-6)烷基、Het和Het-(C1-6)烷基，每种均可选择地用一种或多种取代基取代，每种取代基各自独立地选自卤素、(C1-6)烷基、(C3-7)环烷基、芳基、Het、羟基、-O-(C1-6)烷基、-S-(C1-6)烷基、-SO-(C1-6)烷基、-SO2-(C1-6)烷基、-O-芳基、-S-芳基、-SO-芳基和-SO2-芳基，其中-O-芳基、-S-芳基、-SO-芳基和-SO2-芳基的芳基部分可选择地用一到五个卤素取代基取代。本发明还涉及含有式(I)化合物的药物组合物以及在治疗HCV感染中使用这些类似物的方法。
• Process for the preparation of substituted pyrimidines
  申请人：Lonza AG

  公开号：US05840892A1

  公开（公告）日：1998-11-24

  A novel process for the preparation of substituted pyrimidine derivatives of the general formula: ##STR1## in which a halopyrimidine is reacted in the presence of a sulfinate with a compound selected from the series: ##STR2## The compounds of the general formula I are precursors of, for example, compounds with herbicidal activity.

  一种用于制备通式为：##STR1## 的取代嘧啶衍生物的新工艺，在该工艺中，卤代嘧啶在亚磺酸盐的存在下与选自以下系列化合物之一发生反应：##STR2## 通式I的化合物是例如具有除草活性的化合物的前体。
• Effect of aggregation on stereochemistry and mechanism of asymmetric oxidation of the lithium enolate of methyl 3,3-dimethylbutanoate in the solid state and in solution
  作者：Wei Yen、R. Bakthavatchalam、Jin Xian-Ming、Christopher K. Murphy、Franklin A. Davis

  DOI：10.1016/s0040-4039(00)79208-2

  日期：1993.6

  Oxidation of the title enolate by enantiopure (camphorylsulfonyl)oxaziridines in THF afforded α-hydroxyester with 53–73% ee, but the product from the solid state reactions was racemic. The results suggest that the enolate exists and reacts as an aggregate in the solid state reactions.

  对映体（樟脑磺酰基）恶氮丙啶在THF中氧化标题烯醇化物可得到ee值为53-73％的α-羟基酯，但固态反应的产物是外消旋的。结果表明，烯醇化物以固态反应形式存在并以聚集体形式反应。
• Enantioselective Total Synthesis of (−)-Incarviatone A
  作者：Benke Hong、Chao Li、Zhen Wang、Jie Chen、Houhua Li、Xiaoguang Lei

  DOI：10.1021/jacs.5b08551

  日期：2015.9.23

  We report herein the first total synthesis of (-)-incarviatone A (1) in 14 steps starting from commercially available inexpensive phenylacetic acid (9). Our early stage synthesis relies on the scalable and sequential C-H functionalization to rapidly assemble the indanyl dialdehyde framework. Further biomimetic cascade strategy allows us to obtain the natural product in a one-pot operation. We also

  我们在此报告了 (-)-incarviatone A (1) 的首次全合成，从市售的廉价苯乙酸 (9) 开始，分 14 个步骤。我们的早期合成依赖于可扩展和顺序的 CH 功能化来快速组装茚满二醛框架。进一步的仿生级联策略使我们能够在一锅操作中获得天然产物。我们还进行了详细的机理研究，并公开了在仿生级联过程中形成的所有可能的中间体和异构体。