5-{2-[(S)-2-(2,2-Dimethyl-propionylamino)-8-ethoxyoxalyl-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-yl]-ethyl}-4-methyl-thiophene-2-carboxylic acid | 887149-23-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 5-{2-[(S)-2-(2,2-Dimethyl-propionylamino)-8-ethoxyoxalyl-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-yl]-ethyl}-4-methyl-thiophene-2-carboxylic acid
• 英文别名: 5-[2-[(6S)-2-(2,2-dimethylpropanoylamino)-8-(2-ethoxy-2-oxoacetyl)-4-oxo-3,5,6,7-tetrahydropyrido[2,3-d]pyrimidin-6-yl]ethyl]-4-methylthiophene-2-carboxylic acid
• CAS: 887149-23-7
• 化学式: C₂₄H₃₀N₄O₇S
• 分子量: 518.591
• InChiKey: YTWBXEBSNUBRSO-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  183
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-{2-[(S)-2-(2,2-Dimethyl-propionylamino)-8-ethoxyoxalyl-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-yl]-ethyl}-4-methyl-thiophene-2-carboxylic acid 在 sodium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 pelitrexol
  参考文献：
  名称：

  Efficient Chemoenzymatic Synthesis of Pelitrexol via Enzymic Differentiation of a Remote Stereocenter

  摘要：

  An efficient chemoenzymatic process is described for the synthesis of pelitrexol, a novel GARFT inhibitor. The remoteness of this molecule's stereocenter in the tetrahydropterin moiety from the terminal carbonyl group provided a significant challenge in synthesis. The introduction of an oxalamic ester adjacent to the stereocenter dramatically enhanced an enzyme's enantioselectivity for hydrolysis at the terminal ester, producing the desired S-acid with high optical purity and yield. The recycling of the "wrong" enantiomer is achieved via a dehydrogenation/hydrogenation strategy.

  DOI：

  10.1021/ol0602755
• 作为产物：
  描述：

  5-{2-[2-(2,2-Dimethyl-propionylamino)-8-ethoxyoxalyl-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-yl]-ethyl}-4-methyl-thiophene-2-carboxylic acid ethyl ester 以42的产率得到5-{2-[(S)-2-(2,2-Dimethyl-propionylamino)-8-ethoxyoxalyl-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-yl]-ethyl}-4-methyl-thiophene-2-carboxylic acid
  参考文献：
  名称：

  Org Lett. 2006, 8, 1653-1655

  摘要：

  DOI：

文献信息

• Efficient Chemoenzymatic Synthesis of Pelitrexol via Enzymic Differentiation of a Remote Stereocenter
  作者：Shanghui Hu、Sean Kelly、Steve Lee、Junhua Tao、Erik Flahive

  DOI：10.1021/ol0602755

  日期：2006.4.1

  An efficient chemoenzymatic process is described for the synthesis of pelitrexol, a novel GARFT inhibitor. The remoteness of this molecule's stereocenter in the tetrahydropterin moiety from the terminal carbonyl group provided a significant challenge in synthesis. The introduction of an oxalamic ester adjacent to the stereocenter dramatically enhanced an enzyme's enantioselectivity for hydrolysis at the terminal ester, producing the desired S-acid with high optical purity and yield. The recycling of the "wrong" enantiomer is achieved via a dehydrogenation/hydrogenation strategy.
• Org Lett. 2006, 8, 1653-1655
  作者：

  DOI：——

  日期：——