(R)-(-)-methyl 2-hydroxy-3-mercaptopropionate | 103004-10-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(-)-methyl 2-hydroxy-3-mercaptopropionate
• 英文别名: methyl (S)-2-hydroxy-3-mercaptopropionate；methyl (2R)-2-hydroxy-3-sulfanylpropanoate
• CAS: 103004-10-0
• 化学式: C₄H₈O₃S
• 分子量: 136.172
• InChiKey: ACAWSWFKTBKJBP-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.55
• 重原子数：
  8.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.53
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  二环己基甲酮 、 (R)-(-)-methyl 2-hydroxy-3-mercaptopropionate 在 对甲苯磺酸 作用下， 以 xylene 为溶剂， 反应 24.0h， 生成 methyl (R)-(-)-2,2-dicyclohexyl-1,3-oxathiolane-5-carboxylate
  参考文献：
  名称：

  Molecular requirements of the recognition site of cholinergic receptors. 27. Enantioselectivity of muscarinic antagonists. 2,2-Dicyclohexyl-5-[(dimethylamino)methyl]-1,3-oxathiolane methiodides and related 3-oxides

  摘要：

  The enantiomers of three chiral muscarinic antagonists carrying a 1,3-oxathiolane nucleus were prepared and their absolute configuration established. The enantioselectivity and tissue selectivity of such compounds were studied on rat bladder and guinea pig ileum and heart. The results show that introduction of a sulfoxide function brings about a small but definite enantioselectivity in the 1,3-oxathiolane compound (2), which in itself does not show enantioselectivity among the tissues studied. The results obtained point to differences among cardiac and ileal muscarinic receptors. Comparison of the absolute configuration related agonists shows that the most potent isomers of both series share the same absolute stereochemistry.

  DOI：

  10.1021/jm00117a006
• 作为产物：
  描述：

  (2S)-甘油酸甲酯 在 sodium hydride 、 三乙基硅烷 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (R)-(-)-methyl 2-hydroxy-3-mercaptopropionate
  参考文献：
  名称：

  (±)-Spiroaxillarone A 通过可逆 Sulfa-Michael 加成的全合成

  摘要：

  描述了一种用于全合成螺菌酮 A 的仿生策略，该策略对耐药性恶性疟原虫具有显着的抗疟活性(IC 50 = 2.32 μM)。关键步骤包括分子间乙硫醇迈克尔加成、邻醌迈克尔加成和随后的 β-乙硫醇消除。该合成序列提供了螺菌酮 A 的潜在生物合成途径。

  DOI：

  10.1021/acs.orglett.1c04282

文献信息

• Molecular requirements of the recognition site of cholinergic receptors. 22. Resolution, absolute configuration, and cholinergic enantioselectivity of (+)- and (-)-cis-2-methyl-5-[(dimethylamino)methyl]-1,3-oxathiolane methiodide
  作者：Elisabetta Teodori、Fulvio Gualtieri、Piero Angeli、Livio Brasili、Mario Giannella、Maria Pigini

  DOI：10.1021/jm00159a009

  日期：1986.9

  The potent cholinergic agonist (+/-)-cis-2-methyl-5-[(dimethylamino)methyl]-1,3-oxathiolane methiodide (+/-)-1] was resolved into enantiomeric forms. Their absolute configurations were established by a synthetic pathway that also allowed the synthesis of the corresponding diastereomeric (+)- and (-)-trans-2-methyl-5-[(dimethylamino)-methyl]-1,3-oxathiolane methiodide [(+)- and (-)-10]. Compound (+)-1, which is the most potent of the four isomers, showed the same absolute configuration as L-(+)-muscarine and (+)-cis-dioxolane. The four isomers were tested on guinea pig ileum and frog rectus abdominis, and their muscarinic and nicotinic potency (EPMR) and selectivity were determined. The relationships between stereoisomerism and potency are discussed.
• TEODORI E.; GUALTIERI F.; ANGELI P.; BRASILI L.; GIANNELLA M.; PIGINI M., J. MED. CHEM., 29,(1986) N 9, 1610-1615
  作者：TEODORI E.、 GUALTIERI F.、 ANGELI P.、 BRASILI L.、 GIANNELLA M.、 PIGINI M.

  DOI：——

  日期：——
• ROMANELLI, M. NOVELLA;TEODORI, ELISABETTA;GUALTIERI, FULVIO;ANGELI, PIERO+, J. MED. CHEM., 31,(1988) N 9, C. 1698-1702
  作者：ROMANELLI, M. NOVELLA、TEODORI, ELISABETTA、GUALTIERI, FULVIO、ANGELI, PIERO+

  DOI：——

  日期：——
• Total Synthesis of (±)-Spiroaxillarone A via a Reversible Sulfa-Michael Addition
  作者：Xianwen Long、Min Zhang、Xiaodong Yang、Jun Deng

  DOI：10.1021/acs.orglett.1c04282

  日期：2022.2.18

  A bioinspired strategy is described for the total synthesis of spiroaxillarone A, which exhibited significant antimalarial activity against resistant Plasmodium falciparum (IC50 = 2.32 μM). The key steps include an intermolecular ethanethiol Michael addition, o-quinone Michael addition, and subsequent β-ethanethiol elimination. This synthetic sequence provides a potential biosynthetic pathway of spiroaxillarone

  描述了一种用于全合成螺菌酮 A 的仿生策略，该策略对耐药性恶性疟原虫具有显着的抗疟活性(IC 50 = 2.32 μM)。关键步骤包括分子间乙硫醇迈克尔加成、邻醌迈克尔加成和随后的 β-乙硫醇消除。该合成序列提供了螺菌酮 A 的潜在生物合成途径。
• Molecular requirements of the recognition site of cholinergic receptors. 27. Enantioselectivity of muscarinic antagonists. 2,2-Dicyclohexyl-5-[(dimethylamino)methyl]-1,3-oxathiolane methiodides and related 3-oxides
  作者：M. Novella Romanelli、Elisabetta Teodori、Fulvio Gualtieri、Piero Angeli、Livio Brasili

  DOI：10.1021/jm00117a006

  日期：1988.9

  The enantiomers of three chiral muscarinic antagonists carrying a 1,3-oxathiolane nucleus were prepared and their absolute configuration established. The enantioselectivity and tissue selectivity of such compounds were studied on rat bladder and guinea pig ileum and heart. The results show that introduction of a sulfoxide function brings about a small but definite enantioselectivity in the 1,3-oxathiolane compound (2), which in itself does not show enantioselectivity among the tissues studied. The results obtained point to differences among cardiac and ileal muscarinic receptors. Comparison of the absolute configuration related agonists shows that the most potent isomers of both series share the same absolute stereochemistry.