(S)-N-[(tert-butoxy)carbonyl]-γ-(2-amino-6-chloropurin-9-yl)-β-homoalanin benzyl ester | 517877-41-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-N-[(tert-butoxy)carbonyl]-γ-(2-amino-6-chloropurin-9-yl)-β-homoalanin benzyl ester
• 英文别名: (S)-Benzyl 4-(2-amino-6-chloro-9H-purin-9-yl)-3-((tert-butoxycarbonyl)amino)butanoate；benzyl (3S)-4-(2-amino-6-chloropurin-9-yl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 517877-41-7
• 化学式: C₂₁H₂₅ClN₆O₄
• 分子量: 460.92
• InChiKey: VUEXWHTZZTVRKN-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  134.25
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (S)-N-[(tert-butoxy)carbonyl]-γ-(2-amino-6-chloropurin-9-yl)-β-homoalanin benzyl ester 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以59%的产率得到(S)-N-[(tert-butoxy)carbonyl]-γ-(guanin-9-yl)-β-homoalanine
  参考文献：
  名称：

  Nucleo--Amino Acids: Synthesis and Oligomerization to -Homoalanyl-PNA

  摘要：

  The synthesis of thyminyl-, uracilyl-, cytosinyl-, and guaninyl-beta(3)-amino acids and the oligomerization of the cytosinyl- and guaninyl-beta(3)-amino acids to beta-homoalanyl-PNA are presented. The pyrimidinyl nucleobases were connected to the gamma-position of beta-homoalanine by Mitsunobu reaction with a beta-homoserine derivative or by nucleophilic substitution of methanesulfonates. For the preparation of the guaninyl-beta(3)-amino acid, a beta-lactam route was established that might be of interest also for the synthesis of other beta(3)-amino acid derivatives. The cytosinyl and guaninyl building blocks were oligomerized to hexamers. They form quite stable self-pairing complexes in H2O as indicated by temperature dependent UV and CD spectroscopy.

  DOI：

  10.1002/1522-2675(200211)85:11<3855::aid-hlca3855>3.0.co;2-a
• 作为产物：
  描述：

  Boc-L-天冬氨酸 4-苄酯 在 N-乙基马来酰亚胺 、 叔-丁基氯甲酸酯 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 264.0h， 生成 (S)-N-[(tert-butoxy)carbonyl]-γ-(2-amino-6-chloropurin-9-yl)-β-homoalanin benzyl ester
  参考文献：
  名称：

  Nucleo--Amino Acids: Synthesis and Oligomerization to -Homoalanyl-PNA

  摘要：

  The synthesis of thyminyl-, uracilyl-, cytosinyl-, and guaninyl-beta(3)-amino acids and the oligomerization of the cytosinyl- and guaninyl-beta(3)-amino acids to beta-homoalanyl-PNA are presented. The pyrimidinyl nucleobases were connected to the gamma-position of beta-homoalanine by Mitsunobu reaction with a beta-homoserine derivative or by nucleophilic substitution of methanesulfonates. For the preparation of the guaninyl-beta(3)-amino acid, a beta-lactam route was established that might be of interest also for the synthesis of other beta(3)-amino acid derivatives. The cytosinyl and guaninyl building blocks were oligomerized to hexamers. They form quite stable self-pairing complexes in H2O as indicated by temperature dependent UV and CD spectroscopy.

  DOI：

  10.1002/1522-2675(200211)85:11<3855::aid-hlca3855>3.0.co;2-a