2,2,2-trichloroethyl (2S,3S)-3-O-[5-2-azido-5-deoxy-2,3-O-(3-pentylidene)-β-D-ribofuranosyl]-2-benzyloxycarbonylamino-3-hydroxybutanoate | 1037307-68-8

• 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: 2,2,2-trichloroethyl (2S,3S)-3-O-[5-2-azido-5-deoxy-2,3-O-(3-pentylidene)-β-D-ribofuranosyl]-2-benzyloxycarbonylamino-3-hydroxybutanoate
• CAS: 1037307-68-8
• 化学式: C₂₄H₃₁Cl₃N₄O₈
• 分子量: 609.891
• InChiKey: YILIDBKAIHZDIA-XSEUIGDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  39.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  150.31
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloroethyl (2S,3S)-3-O-[5-2-azido-5-deoxy-2,3-O-(3-pentylidene)-β-D-ribofuranosyl]-2-benzyloxycarbonylamino-3-hydroxybutanoate 在 三苯基膦 作用下， 以 四氢呋喃 、 水 、 苯 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Structure–activity relationship of truncated analogs of caprazamycins as potential anti-tuberculosis agents

  摘要：

  Systematic structure-activity relationship studies of caprazamycin (CPZ) analogs, including the aminoribose-truncated 5 and the uridine-truncated 6, have been carried out. Both 5 and 6 were synthesized efficiently via diazepanone ring construction by intramolecular reductive alkylation of aminoaldehyde derivatives. The antibacterial activity of a range of analogs, including 5 and 6, against Mycobacteriumosis was evaluated, and it was found that the uridine, the aminoribose, and the fatty acyl side chains are crucial for antibacterial activity. This study would be a guide for designing novel anti-tuberculosis agents based on the 6'-N-alkyl-5'-beta-O-aminoribosyl-glycyluridine class of antibiotics including the CPZs. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.020
• 作为产物：
  描述：

  5-azido-5-deoxy-2,3-O-(3-pentylidene)-D-ribofuranosyl fluoride 、 N-benzyloxycarbonyl-L-threonine 2,2,2-trichloroethyl ester 在 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以84%的产率得到2,2,2-trichloroethyl (2S,3S)-3-O-[5-2-azido-5-deoxy-2,3-O-(3-pentylidene)-β-D-ribofuranosyl]-2-benzyloxycarbonylamino-3-hydroxybutanoate
  参考文献：
  名称：

  Structure–activity relationship of truncated analogs of caprazamycins as potential anti-tuberculosis agents

  摘要：

  Systematic structure-activity relationship studies of caprazamycin (CPZ) analogs, including the aminoribose-truncated 5 and the uridine-truncated 6, have been carried out. Both 5 and 6 were synthesized efficiently via diazepanone ring construction by intramolecular reductive alkylation of aminoaldehyde derivatives. The antibacterial activity of a range of analogs, including 5 and 6, against Mycobacteriumosis was evaluated, and it was found that the uridine, the aminoribose, and the fatty acyl side chains are crucial for antibacterial activity. This study would be a guide for designing novel anti-tuberculosis agents based on the 6'-N-alkyl-5'-beta-O-aminoribosyl-glycyluridine class of antibiotics including the CPZs. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.020