1,3,2',2''',6'''-pentakis-[N-(tert-butoxycarbonyl)]-6',5''-dideoxy-5''-[N-(4-nitrobenzyloxy)imino]paromomycin | 931406-25-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,2',2''',6'''-pentakis-[N-(tert-butoxycarbonyl)]-6',5''-dideoxy-5''-[N-(4-nitrobenzyloxy)imino]paromomycin
• CAS: 931406-25-6
• 化学式: C₅₅H₈₉N₇O₂₅
• 分子量: 1248.34
• InChiKey: JYCGVAGQJNMWSG-LCMSSAEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  87.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  433.14
• 氢给体数：
  11.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  1,3,2',2''',6'''-pentakis-[N-(tert-butoxycarbonyl)]-6',5''-dideoxy-5''-[N-(4-nitrobenzyloxy)imino]paromomycin 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以88%的产率得到1,3,2',2''',6'''-pentakis-[N-(tert-butoxycarbonyl)]-6',5''-dideoxy-5''-[N-(4-aminobenzyloxy)imino]paromomycin
  参考文献：
  名称：

  Synthesis of paromomycin derivatives modified at C(5″) to selectively target bacterial rRNA

  摘要：

  The furanosyl moiety (ring 111) of C(6')-deoxyparomomycin and paromomycin was modified in search of aminoglycoside antibiotics with altered selectivity. The key intermediates were the N-Boc-protected derivative of C(6')-deoxyparomomycin and the benzylidene-protected paromomycin. Their H2C(5")-OH group was oxidised with trichlorocyanuric acid or [bis(acetoxy)iodo]benzene in the presence of catalytic amounts of TEMPO to yield the corresponding aldehydes and acids, which were transformed into the protected alkoxy imines, amides and the amine. Standard deprotection gave the title compounds derived from C(6')-deoxyparomomycin and derived from paromomycin that proved less active than paromomycin and its C(6')-deoxy analogue. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.09.014
• 作为产物：
  描述：

  、 4-硝基苄基羟胺盐酸盐 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 三氯异氰尿酸 、 吡啶 作用下， 以 乙酸乙酯 、 甲醇 为溶剂， 反应 24.0h， 以62%的产率得到1,3,2',2''',6'''-pentakis-[N-(tert-butoxycarbonyl)]-6',5''-dideoxy-5''-[N-(4-nitrobenzyloxy)imino]paromomycin
  参考文献：
  名称：

  Synthesis of paromomycin derivatives modified at C(5″) to selectively target bacterial rRNA

  摘要：

  The furanosyl moiety (ring 111) of C(6')-deoxyparomomycin and paromomycin was modified in search of aminoglycoside antibiotics with altered selectivity. The key intermediates were the N-Boc-protected derivative of C(6')-deoxyparomomycin and the benzylidene-protected paromomycin. Their H2C(5")-OH group was oxidised with trichlorocyanuric acid or [bis(acetoxy)iodo]benzene in the presence of catalytic amounts of TEMPO to yield the corresponding aldehydes and acids, which were transformed into the protected alkoxy imines, amides and the amine. Standard deprotection gave the title compounds derived from C(6')-deoxyparomomycin and derived from paromomycin that proved less active than paromomycin and its C(6')-deoxy analogue. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.09.014