(5S,7S)-5-((R)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-5,8a-dimethyl-octahydro-furo[2,3-d]pyrrolo[2,1-b]thiazole-7-carboxylic acid ethyl ester | 512169-57-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: (5S,7S)-5-((R)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-5,8a-dimethyl-octahydro-furo[2,3-d]pyrrolo[2,1-b]thiazole-7-carboxylic acid ethyl ester
• CAS: 512169-57-2
• 化学式: C₂₄H₃₀N₂O₆S
• 分子量: 474.578
• InChiKey: LRKDDRKARDDUMG-KUCWZKDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  85.38
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (5S,7S)-5-((R)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-5,8a-dimethyl-octahydro-furo[2,3-d]pyrrolo[2,1-b]thiazole-7-carboxylic acid ethyl ester 在 silver trifluoromethanesulfonate 、 phosphate buffer 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-((R)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-4-methyl-3,4-dihydro-2H-pyrrole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Methylation of l-trans-2,4-Pyrrolidine Dicarboxylate Converts the Glutamate Transport Inhibitor from a Substrate to a Non-substrate Inhibitor

  摘要：

  The 4-methyl analogue of the potent inhibitor of CNS L-glutamate neurotransmitter transporters, L-trans-2,4-PDC, was synthesized via a 1,3-dipolar cycloaddition reaction sequence. The bioassays performed not only exhibit increased potency of the methylated derivative over L-trans-2,4-PDC, but also exhibit non-substrate properties at the rat forebrain synaptosomal glutamate transporter while the parent L-trans-2,4-PDC exhibits substrate properties. These results support two hypotheses developed for distinguishing the physiological properties of transport inhibitors based on molecular modeling studies, and are reported here. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00250-x
• 作为产物：
  描述：

  3-(Ethoxycarbonylmethyl)-5-(2-hydroxyethyl)-4-methylthiazolium Bromide 、 (4R)-3-(2-methyl-2-propenoyl)-4-(phenylmethyl)-2-oxazolidinone 在 4 A molecular sieve 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 (5S,7S)-5-((R)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-5,8a-dimethyl-octahydro-furo[2,3-d]pyrrolo[2,1-b]thiazole-7-carboxylic acid ethyl ester
  参考文献：
  名称：

  Methylation of l-trans-2,4-Pyrrolidine Dicarboxylate Converts the Glutamate Transport Inhibitor from a Substrate to a Non-substrate Inhibitor

  摘要：

  The 4-methyl analogue of the potent inhibitor of CNS L-glutamate neurotransmitter transporters, L-trans-2,4-PDC, was synthesized via a 1,3-dipolar cycloaddition reaction sequence. The bioassays performed not only exhibit increased potency of the methylated derivative over L-trans-2,4-PDC, but also exhibit non-substrate properties at the rat forebrain synaptosomal glutamate transporter while the parent L-trans-2,4-PDC exhibits substrate properties. These results support two hypotheses developed for distinguishing the physiological properties of transport inhibitors based on molecular modeling studies, and are reported here. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00250-x