(2S,3R)-2-chloro-3-hydroxypropionic acid | 134267-57-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (2S,3R)-2-chloro-3-hydroxypropionic acid
• 英文别名: (S)-2-chloro-3-hydroxypropionic acid；(s)-2-Chloro-3-hydroxypropanoic acid；(2S)-2-chloro-3-hydroxypropanoic acid
• CAS: 134267-57-5
• 化学式: C₃H₅ClO₃
• 分子量: 124.524
• InChiKey: GAHMZBZGINHHJR-REOHCLBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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-chloro-3-hydroxypropionic acid 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以70%的产率得到(R)-环氧乙烷-2-羧酸钾
  参考文献：
  名称：

  Aromatic sulfonyl alpha-hydroxy hydroxamic acid compounds

  摘要：

  本文披露了一种具有芳香基的磺酰基α-羟基羟肟酸化合物，该化合物等方面抑制基质金属蛋白酶活性，以及一种治疗过程，包括向患有与病理性基质金属蛋白酶活性相关病症的宿主施用考虑中的芳香基磺酰基α-羟基羟肟酸化合物，其剂量有效地抑制MMP酶活性。

  公开号：

  US06362183B1
• 作为产物：
  描述：

  L-丝氨酸 在 盐酸 、 sodium nitrite 作用下， 以97%的产率得到
  参考文献：
  名称：

  双塞内酯A的全合成

  摘要：

  描述了海洋大环内酯双己内酯 A 的全合成，其依赖于对映体富集的 α-氯醛作为唯一的手性结构单元。提出了构建大环的几种策略，包括大环 Reformatsky 反应，该反应最终以 18 个步骤的最长线性序列提供天然产物。合成双塞内酯 A 的生物学测试表明，这种大环内酯通过与微管细胞骨架组织调节相关的机制破坏细胞分裂。总的来说，这种简明的合成和对作用机制的深入了解应该会激发针对结构相关的抗癌海洋大环内酯的药物化学研究。

  DOI：

  10.1039/d0sc06223e

文献信息

• Synthesis of Optically Active N6-Alkyl Derivatives of (R)-3-(Adenin-9-yl)-2-hydroxypropanoic Acid and Related Compounds
  作者：Marcela Krečmerová、Miloš Buděšínský、Milena Masojídková、Antonín Holý

  DOI：10.1135/cccc20030931

  日期：——

  Reaction of ethyl (R)-oxiranecarboxylate (2a) with various nucleobases (adenine, 6-chloropurine, thymine, cytosine, N⁶-benzoyladenine, 4-methoxy-5-methylpyrimidin-2(1H)-one and 4-methoxypyrimidin-2(1H)-one) afforded ethyl 3-substituted-2-hydroxypropanoates 4-10. Enantioselectivity of this reaction is dependent on the type of the base: 6-chloropurine, N⁶-benzoyladenine, 4-methoxy-5-methylpyrimidin-2(1H)-one, thymine and cytosine gave optically pure R enantiomers. In other cases, partial or complete racemization occurred. Optically pure ethyl (R)-3-(6-chloropurin-9-yl)-2-hydroxypropanoate (5a) was hydrolyzed to give (R)-3-(6-chloropurin-9-yl)-2-hydroxypropanoic acid (11). Reactions of 11 with various primary or secondary amines led to N⁶-substituted (R)-3-(adenin-9-yl)-2-hydroxypropanoic acids 14-19. Enantiomeric purity was determined from ¹H NMR spectra measured in the presence of (-)-(R)-1-(9-anthryl)-2,2,2-trifluoroethan-1-ol.

  乙基（R）-环氧丙酸乙酯（2a）与各种核碱基（腺嘌呤、6-氯嘌呤、胸腺嘧啶、胞嘧啶、N6-苯甲酰腺嘌呤、4-甲氧基-5-甲基嘧啶-2（1H）-酮和4-甲氧基嘧啶-2（1H）-酮）反应生成乙基3-取代-2-羟基丙酸酯4-10。该反应的对映选择性取决于碱基的类型：6-氯嘌呤、N6-苯甲酰腺嘌呤、4-甲氧基-5-甲基嘧啶-2（1H）-酮、胸腺嘧啶和胞嘧啶生成光学纯R对映异构体。在其他情况下，部分或完全消旋发生。光学纯乙基（R）-3-（6-氯嘌呤-9-基）-2-羟基丙酸酯（5a）水解得到（R）-3-（6-氯嘌呤-9-基）-2-羟基丙酸（11）。11与各种一级或二级胺的反应导致N6-取代（R）-3-（腺嘌呤-9-基）-2-羟基丙酸14-19。对映纯度是通过在(-)-（R）-1-（9-蒽基）-2,2,2-三氟乙醇存在下测定的1H NMR谱来确定的。
• Esterase Catalyzed Regio- and Enantio-selective Hydrolysis of Substituted Carboxylates
  作者：Eiji Ozaki、Keiichi Sakashita

  DOI：10.1246/cl.1997.741

  日期：1997.8

  Optically active α-substituted carboxylic acid derivatives were obtained with regio- and enantio-selective hydrolysis catalyzed by esterase from Pseudomonas putida MR-2068. Substrate specificities were summarized in empirical rule to predict the enantiopreferences of the esterase. High regio-selectivities were also discussed with binding models.

  通过恶臭假单胞菌 MR-2068 的酯酶催化区域选择性和对映选择性水解，获得光学活性 α-取代的羧酸衍生物。底物特异性总结为经验规则，以预测酯酶的对映体优先性。还讨论了结合模型的高区域选择性。
• Enantioselective synthesis of 2-alkyl-5-methylene-1,3-dioxolan-4-ones and exo-selective Diels-Alder reactions with cyclopentadiene
  作者：William R. Roush、Bradley B. Brown

  DOI：10.1021/jo00038a028

  日期：1992.6

  Highly stereoselective syntheses of chiral dienophiles (R)-1 and (R)-2 are described. Diazotization of L-serine in the presence of HCI and then treatment of the resulting beta-hydroxy-alpha-chloropropionic acid (S)-7 with KOH provides potassium glycidate ((R)-8) in good yield and high enantiomeric purity. Treatment of (R)-8 with PhSH in MeOH then provides alpha-hydroxy acid (S)-10 that can be purified by recrystallization. Condensation of (S)-10 with either pivalaldehyde or cyclohexanecarboxaldehyde followed by oxidation to the sulfone and DBU-promoted elimination of benzenesulfinic acid then provides dienophiles (R)-1 and (R)-2, respectively. Highly exo-selective Diels-Alder reactions of (R)-1 and (R)-2 with cyclopentadiene are also described. The major cycloadduct (-)-15 (94% of total) from the Diels-Alder reaction of 1 was shown to have an enantiomeric purity of greater-than-or-equal-to 99% ee. This figure defines the lower limit of enantiomeric purity of (R)-1. The diastereofacial selectivity of the Diels-Alder reactions of 1 in the exo manifold (50:1) is greater than that of 2 (20:1), as would be expected on the basis of the different steric requirements of the tert-butyl and cyclohexyl substituents of the two reagents. Consequently, dienophile 1 is the preferred reagent for complex synthetic applications, either as a chiral ketene equivalent or in contexts in which the a-hydroxy acid functionality will be preserved in the ultimate synthetic target. Finally, the possible role of dipole effects on the exo selectivity of the Diels-Alder reactions of these and related dienophiles are briefly discussed.