1,3,2',6',3''-pentakis(N-benzyloxycarbonyl)-3'-deoxykanamycin B | 61093-69-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,2',6',3''-pentakis(N-benzyloxycarbonyl)-3'-deoxykanamycin B
• 英文别名: benzyl N-[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-[(1S,2S,3R,4S,6R)-2-hydroxy-3-[(2R,3R,5S,6R)-5-hydroxy-3-(phenylmethoxycarbonylamino)-6-(phenylmethoxycarbonylaminomethyl)oxan-2-yl]oxy-4,6-bis(phenylmethoxycarbonylamino)cyclohexyl]oxy-6-(hydroxymethyl)oxan-4-yl]carbamate
• CAS: 61093-69-4
• 化学式: C₅₈H₆₇N₅O₁₉
• 分子量: 1138.19
• InChiKey: LLYYNJWDZOMLGA-STJVHCRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  82.0
• 可旋转键数：
  21.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  329.72
• 氢给体数：
  10.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  1,3,2',6',3''-pentakis(N-benzyloxycarbonyl)-3'-deoxykanamycin B 在 palladium on activated charcoal 吡啶 、 sodium tetrahydroborate 、 氢气 、 sodium methylate 、 sodium hydride 、 臭氧 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 2.83h， 生成
  参考文献：
  名称：

  Tobramycin analogues with C-5 aminoalkyl ether chains intended to mimic rings III and IV of paromomycin

  摘要：

  Based on available X-ray structural and modeling data, a series of tobramycin derivatives with C-5 ether chains bearing basic groups were synthesized. These were intended to be hybrid molecules that combine features of tobramycin and paromomycin. Their binding to ribosomes and their antibacterial activity were determined. The 5-O-(2-guanidylethyl) ether of tobramycin (9g) was the most active analogue in the series. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01624-1
• 作为产物：
  描述：

  氯甲酸苄酯 、 硫酸妥布霉素 在 sodium carbonate 作用下， 以 水 、 丙酮 为溶剂， 以96%的产率得到1,3,2',6',3''-pentakis(N-benzyloxycarbonyl)-3'-deoxykanamycin B
  参考文献：
  名称：

  Synthesis of 5-deoxy-5-fluoro and 5-deoxy-5,5-difluoro derivatives of kanamycin B in its analogs. Study on structure-toxicity relationships

  摘要：

  5-Deoxy-5-fluoro- (1), 5,3'-dideoxy-5-fluoro- (2), and 5,3',4'-trideoxy-5-fluoro-kanamycin B (3) have been prepared by treatment of 5-epihydroxyl precursors (prepared by the Mitsunobu reaction) with DAST as the key step. 5,3'-Dideoxy-5,5-difluoro- (26) and 5,3',4'-trideoxy-5,5-difluoro-kanamycin B (27) were also prepared by treatment of the corresponding 5-oxo derivatives with DAST. These 5-deoxy-5-fluoro and 5-deoxy-5,5-difluoro derivatives showed markedly decreased toxicity as compared with the parent compounds.

  DOI：

  10.1016/0008-6215(92)80060-e

文献信息

• Dimeric aminoglycosides: Design, synthesis and RNA binding
  作者：Hai Wang、Yitzhak Tor

  DOI：10.1016/s0960-894x(97)00339-9

  日期：1997.7

  The design and synthesis of symmetrical and non-symmetrical dimeric aminoglycosides derived from kanamycin A, tobramycin, and neomycin B are described. The covalently-linked dimeric aminoglycosides show enhanced activity as ribozyme inhibitors when compared to their natural counterparts. (C) 1997 Elsevier Science Ltd.
• RNA–Aminoglycoside Interactions: Design, Synthesis, and Binding of “Amino-aminoglycosides” to RNA
  作者：Hai Wang、Yitzhak Tor

  DOI：10.1002/(sici)1521-3773(19980202)37:1/2<109::aid-anie109>3.0.co;2-0

  日期：1998.2.2