1,3,2',2''',6'''-pentakis-[N-(tert-butoxycarbonyl)]-6'-deoxy-5''-carboxyparomomycin | 931406-31-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,2',2''',6'''-pentakis-[N-(tert-butoxycarbonyl)]-6'-deoxy-5''-carboxyparomomycin
• CAS: 931406-31-4
• 化学式: C₄₈H₈₃N₅O₂₄
• 分子量: 1114.21
• InChiKey: YGPFUXCFHRMQAA-QEFIXTORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.09
• 重原子数：
  77.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  405.71
• 氢给体数：
  12.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  1,3,2',2''',6'''-pentakis-[N-(tert-butoxycarbonyl)]-6'-deoxy-5''-carboxyparomomycin 、 苄胺 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 以45%的产率得到1,3,2',2''',6'''-pentakis-[N-(tert-butoxycarbonyl)]-6'-deoxy-5''-(N-benzyl)paromomycincarboxamide
  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：

  在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘苯二乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 以54%的产率得到1,3,2',2''',6'''-pentakis-[N-(tert-butoxycarbonyl)]-6'-deoxy-5''-carboxyparomomycin
  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