(R)-tert-Butoxycarbonylamino-((1S,3R)-3-hydroxy-cyclopentyl)-acetic acid methyl ester | 677781-90-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-tert-Butoxycarbonylamino-((1S,3R)-3-hydroxy-cyclopentyl)-acetic acid methyl ester
• 英文别名: methyl (2R)-2-[(1S,3R)-3-hydroxycyclopentyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 677781-90-7
• 化学式: C₁₃H₂₃NO₅
• 分子量: 273.329
• InChiKey: SVURYPUFUJFXIV-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-tert-Butoxycarbonylamino-((1S,3R)-3-hydroxy-cyclopentyl)-acetic acid methyl ester 在 lithium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 三乙胺 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3-Fluoro-phenyl)-carbamic acid (1R,3S)-3-((R)-1-tert-butoxycarbonylamino-2-oxo-2-thiazolidin-3-yl-ethyl)-cyclopentyl ester
  参考文献：
  名称：

  Diastereoselective synthesis and configuration-dependent activity of (3-substituted-cycloalkyl)glycine pyrrolidides and thiazolidides as dipeptidyl peptidase IV inhibitors

  摘要：

  A diastereoselective synthesis was used to prepare a series of (3-substituted-cyclopentyl and -cyclohexyl)glycine pyrrolidides and thiazolidides. The three chiral centers were generated in an unambiguous, stereochemically defined manner. Inhibitory activity was dependent on the configuration at each stereocenter and on the nature of the 3-substituent. In the cyclopentylglycine pyrrolidide series, high potency against dipeptidyl peptidase IV and good selectivity could be achieved. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.013
• 作为产物：
  描述：

  (3S)-3-[(2S,5R)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]cyclopentan-1-one 在 盐酸 、 sodium tetrahydroborate 、 sodium methylate 、 sodium carbonate 、 sodium chloride 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 (R)-tert-Butoxycarbonylamino-((1S,3R)-3-hydroxy-cyclopentyl)-acetic acid methyl ester
  参考文献：
  名称：

  Diastereoselective synthesis and configuration-dependent activity of (3-substituted-cycloalkyl)glycine pyrrolidides and thiazolidides as dipeptidyl peptidase IV inhibitors

  摘要：

  A diastereoselective synthesis was used to prepare a series of (3-substituted-cyclopentyl and -cyclohexyl)glycine pyrrolidides and thiazolidides. The three chiral centers were generated in an unambiguous, stereochemically defined manner. Inhibitory activity was dependent on the configuration at each stereocenter and on the nature of the 3-substituent. In the cyclopentylglycine pyrrolidide series, high potency against dipeptidyl peptidase IV and good selectivity could be achieved. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.013