diethyl 1-[(1R,2R,3R,4R)-3-(tert-butoxycarbonylamino)-4-(ethoxycarbonyl)-2-hydroxycyclopentyl]-1H-1,2,3-triazole-4,5-dicarboxylate | 1137738-58-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: diethyl 1-[(1R,2R,3R,4R)-3-(tert-butoxycarbonylamino)-4-(ethoxycarbonyl)-2-hydroxycyclopentyl]-1H-1,2,3-triazole-4,5-dicarboxylate
• 英文别名: diethyl 1-[(1R,2R,3R,4R)-4-ethoxycarbonyl-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentyl]triazole-4,5-dicarboxylate
• CAS: 1137738-58-9
• 化学式: C₂₁H₃₂N₄O₉
• 分子量: 484.506
• InChiKey: ONHCSTFCQBJZGM-JXFSHQFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  168
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  ethyl (1R,2R,3R,4R)-4-azido-2-(tert-butoxycarbonylamino)-3-hydroxycyclopentane-1-carboxylate 、 丁炔二酸二乙酯 以 乙醇 为溶剂， 反应 6.0h， 以69%的产率得到diethyl 1-[(1R,2R,3R,4R)-3-(tert-butoxycarbonylamino)-4-(ethoxycarbonyl)-2-hydroxycyclopentyl]-1H-1,2,3-triazole-4,5-dicarboxylate
  参考文献：
  名称：

  Novel functionalized cispentacin derivatives. Synthesis of 1,2,3-triazole-substituted 2-aminocyclopentanecarboxylate stereoisomers

  摘要：

  Four 1,2,3-triazole-substituted ethyl 2-amino-3-hydroxycyclopentanecarboxylate diastereomers (3,4-disubstituted cispentacins) with a cyclopentane skeleton were prepared in enantiomerically pure form from racemic beta-lactam 7 via enzymatic ring opening, epoxidation and selective ring opening of the oxirane ring with sodium azide. The formation of the 1,2,3-triazole ring system involved click chemistry: 1,3-dipolar cycloaddition of the corresponding 4-substituted azidocarboxylates with diethyl acetylenedicarboxylate. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.035