O-4,6-diacetyl-2,3-dideoxy-3-<(trifluoroacetyl)amino>-α-D-glucopyranosyl-(1->6)-O-<2,6-bis<(trifluoroacetyl)amino>-2,3,4,6-tetradeoxy-α-D-glucopyranosyl-(1->4)>-2-deoxy-1,3-bis-N-(trifluoroacetyl)-D-streptamine | 79628-29-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-4,6-diacetyl-2,3-dideoxy-3-<(trifluoroacetyl)amino>-α-D-glucopyranosyl-(1->6)-O-<2,6-bis<(trifluoroacetyl)amino>-2,3,4,6-tetradeoxy-α-D-glucopyranosyl-(1->4)>-2-deoxy-1,3-bis-N-(trifluoroacetyl)-D-streptamine
• 英文别名: O-4,6-diacetyl-2,3-dideoxy-3-[(trifluoroacetyl)amino]-α-D-glucopyranosyl-(1->6)-O-[2,6-bis[(trifluoroacetyl)amino]-2,3,4,6-tetradeoxy-α-D-glucopyranosyl-(1->4)]-2-deoxy-1,3-bis-N-(trifluoroacetyl)-D-streptamine
• CAS: 79628-29-8
• 化学式: C₃₂H₃₆F₁₅N₅O₁₄
• 分子量: 999.639
• InChiKey: XVNDHFILWMZLJY-KZBYXHODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  66.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  255.25
• 氢给体数：
  6.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  O-4,6-diacetyl-2,3-dideoxy-3-<(trifluoroacetyl)amino>-α-D-glucopyranosyl-(1->6)-O-<2,6-bis<(trifluoroacetyl)amino>-2,3,4,6-tetradeoxy-α-D-glucopyranosyl-(1->4)>-2-deoxy-1,3-bis-N-(trifluoroacetyl)-D-streptamine 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以86.5%的产率得到2",3',4'-trideoxykanamycin B
  参考文献：
  名称：

  Chemical modification of aminoglycosides. 3. Synthesis of 2"-deoxykanamycins from neamine

  摘要：

  The preparation of 2"-deoxykanamycin B (12) and 2",3',4'-trideoxykanamycin B (14) from neamine (1) is described. Key intermediates in the synthesis of these 2"-deoxyaminoglycoside antibiotics are 3',4'-bis-O-(p-nitrobenzoyl)-1,2',3,6'-tetrakis-N-(trifluoroacetyl)neamine (6) and 3',4'-dideoxy-1,2',3,6'-tetrakis-N-(trifluoroacetyl)neamine (9). The amino groups of these intermediates are blocked by the trifluoroacetyl group, a blocking group not widely used in aminoglycoside chemistry.

  DOI：

  10.1021/jm00144a023
• 作为产物：
  描述：

  3',4'-dideoxy-3'-eno-5,6-O-isopropylidene-1,2',3,6'-tetrakis-N-(trifluoroacetyl)neamine 在 platinum(IV) oxide 三氟化硼乙醚 、 水 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 23.25h， 生成 O-4,6-diacetyl-2,3-dideoxy-3-<(trifluoroacetyl)amino>-α-D-glucopyranosyl-(1->6)-O-<2,6-bis<(trifluoroacetyl)amino>-2,3,4,6-tetradeoxy-α-D-glucopyranosyl-(1->4)>-2-deoxy-1,3-bis-N-(trifluoroacetyl)-D-streptamine
  参考文献：
  名称：

  Chemical modification of aminoglycosides. 3. Synthesis of 2"-deoxykanamycins from neamine

  摘要：

  The preparation of 2"-deoxykanamycin B (12) and 2",3',4'-trideoxykanamycin B (14) from neamine (1) is described. Key intermediates in the synthesis of these 2"-deoxyaminoglycoside antibiotics are 3',4'-bis-O-(p-nitrobenzoyl)-1,2',3,6'-tetrakis-N-(trifluoroacetyl)neamine (6) and 3',4'-dideoxy-1,2',3,6'-tetrakis-N-(trifluoroacetyl)neamine (9). The amino groups of these intermediates are blocked by the trifluoroacetyl group, a blocking group not widely used in aminoglycoside chemistry.

  DOI：

  10.1021/jm00144a023