methyl (2S,5R)-trans-2-methyl-1,3-oxathiolane-5-carboxylate | 103066-67-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧硫杂环戊烷
• 英文名称: methyl (2S,5R)-trans-2-methyl-1,3-oxathiolane-5-carboxylate
• 英文别名: methyl (2S,5R)-2-methyl-1,3-oxathiolane-5-carboxylate
• CAS: 103066-67-7
• 化学式: C₆H₁₀O₃S
• 分子量: 162.21
• InChiKey: OZKHMOLYVGGOPV-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S,5R)-trans-2-methyl-1,3-oxathiolane-5-carboxylate 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 28.0h， 生成 (2S,5R)-trans-2-methyl-5-<(dimethylamino)methyl>-1,3-oxathilane
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jm00159a009
• 作为产物：
  描述：

  (R)-(-)-methyl 2-hydroxy-3-mercaptopropionate 、 乙醛 、 对甲苯磺酸 生成 methyl (2S,5R)-trans-2-methyl-1,3-oxathiolane-5-carboxylate
  参考文献：
  名称：

  TEODORI E.; GUALTIERI F.; ANGELI P.; BRASILI L.; GIANNELLA M.; PIGINI M., J. MED. CHEM., 29,(1986) N 9, 1610-1615

  摘要：

  DOI：

文献信息

• 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：——
• 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.