(2R)-6-N-(tert-butoxycarbonyl)amino-2-benzylhexanoyl-glycyl-glycine ethyl ester | 286965-05-7

• 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: (2R)-6-N-(tert-butoxycarbonyl)amino-2-benzylhexanoyl-glycyl-glycine ethyl ester
• 英文别名: ethyl 2-[[2-[[(2R)-2-benzyl-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]amino]acetyl]amino]acetate
• CAS: 286965-05-7
• 化学式: C₂₄H₃₇N₃O₆
• 分子量: 463.574
• InChiKey: GKWLSXZOFOYIPB-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  33
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R)-6-N-(tert-butoxycarbonyl)amino-2-benzylhexanoyl-glycyl-glycine ethyl ester 在 lithium hydroxide 、 氰基磷酸二乙酯 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 20.0h， 生成 (9R)-9-benzyl-1,4,7-triazacyclotridecane-2,5,8-trione
  参考文献：
  名称：

  Effect of Progressive Benzyl Substitution on the Conformations of Aminocaproic Acid-Cyclized Dipeptides

  摘要：

  The constraint of dipeptides into a beta -turn conformation can be accomplished by linking the two ends of a standard dipeptide with a linker derived from aminocaproic acid (Aca). To elucidate the possibility of using substituted Aca linkers in peptidomimetic design, a series of five macrocycles composed of a monobenzylated Aca linker (containing the benzyl group on each of the five methylene groups of the parent linker) and Gly-Gly were synthesized. The requisite linkers were made by regiochemically controlled ring expansion techniques (for substitution on Aca positions C-3, C-4, or C-5), an Evans alkylation route (for C-2), or by chain extension of L-phenylalanal (for C-6). The solution-phase conformations of the macrocycles were examined by NMR and CD techniques; in addition, crystal structures of the C-4- and C-6-benzyl-substituted linkers were obtained. Four out of the five macrocycles were found to exist with the dipeptide portion taking up either a type II or II ' beta -turn conformation, but the Gly-Gly unit in the compound derived from 4-benzyl-Aca did not correspond to one of the standard beta -turn types.

  DOI：

  10.1021/jo001308b
• 作为产物：
  描述：

  6-溴己酰氯 在 palladium dihydroxide 三乙基硅烷 、 lithium hydroxide 、 正丁基锂 、 sodium azide 、 双氧水 、 sodium hexamethyldisilazane 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.92h， 生成 (2R)-6-N-(tert-butoxycarbonyl)amino-2-benzylhexanoyl-glycyl-glycine ethyl ester
  参考文献：
  名称：

  Effect of Progressive Benzyl Substitution on the Conformations of Aminocaproic Acid-Cyclized Dipeptides

  摘要：

  The constraint of dipeptides into a beta -turn conformation can be accomplished by linking the two ends of a standard dipeptide with a linker derived from aminocaproic acid (Aca). To elucidate the possibility of using substituted Aca linkers in peptidomimetic design, a series of five macrocycles composed of a monobenzylated Aca linker (containing the benzyl group on each of the five methylene groups of the parent linker) and Gly-Gly were synthesized. The requisite linkers were made by regiochemically controlled ring expansion techniques (for substitution on Aca positions C-3, C-4, or C-5), an Evans alkylation route (for C-2), or by chain extension of L-phenylalanal (for C-6). The solution-phase conformations of the macrocycles were examined by NMR and CD techniques; in addition, crystal structures of the C-4- and C-6-benzyl-substituted linkers were obtained. Four out of the five macrocycles were found to exist with the dipeptide portion taking up either a type II or II ' beta -turn conformation, but the Gly-Gly unit in the compound derived from 4-benzyl-Aca did not correspond to one of the standard beta -turn types.

  DOI：

  10.1021/jo001308b