O-2,6-dideoxy-2,6-bis<(trifluoroacetyl)amino>-3,4-bis-O-(p-nitrobenzoyl)-α-D-glucopyranosyl-(1->4)-O-<4,6-O-diacetyl-2,3-dideoxy-3-<(trifluoroacetyl)amino>-α-D-glucopyranosyl-(1->6)>-2-deoxy-1,3-bis-N-(trifluoroacetyl)-D-streptamine | 79633-99-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-2,6-dideoxy-2,6-bis<(trifluoroacetyl)amino>-3,4-bis-O-(p-nitrobenzoyl)-α-D-glucopyranosyl-(1->4)-O-<4,6-O-diacetyl-2,3-dideoxy-3-<(trifluoroacetyl)amino>-α-D-glucopyranosyl-(1->6)>-2-deoxy-1,3-bis-N-(trifluoroacetyl)-D-streptamine
• 英文别名: O-2,6-dideoxy-2,6-bis[(trifluoroacetyl)amino]-3,4-bis-O-(p-nitrobenzoyl)-α-D-glucopyranosyl-(1->4)-O-{4,6-O-diacetyl-2,3-dideoxy-3-[(trifluoroacetyl)amino]-α-D-glucopyranosyl-(1->6)}-2-deoxy-1,3-bis-N-(trifluoroacetyl)-D-streptamine
• CAS: 79633-99-1
• 化学式: C₄₆H₄₂F₁₅N₇O₂₂
• 分子量: 1329.85
• InChiKey: FECDROZPTLAOAB-QEWSFVTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  90.0
• 可旋转键数：
  19.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  394.13
• 氢给体数：
  6.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  O-2,6-dideoxy-2,6-bis<(trifluoroacetyl)amino>-3,4-bis-O-(p-nitrobenzoyl)-α-D-glucopyranosyl-(1->4)-O-<4,6-O-diacetyl-2,3-dideoxy-3-<(trifluoroacetyl)amino>-α-D-glucopyranosyl-(1->6)>-2-deoxy-1,3-bis-N-(trifluoroacetyl)-D-streptamine 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.17h， 以57.5%的产率得到2"-deoxykanamycin 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：

  5,6-isopropylidene-1,2',3,6'-tetrakis-N-(trifluoroacetyl)neamine 在 吡啶 、 三氟化硼乙醚 、 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 反应 11.5h， 生成 O-2,6-dideoxy-2,6-bis<(trifluoroacetyl)amino>-3,4-bis-O-(p-nitrobenzoyl)-α-D-glucopyranosyl-(1->4)-O-<4,6-O-diacetyl-2,3-dideoxy-3-<(trifluoroacetyl)amino>-α-D-glucopyranosyl-(1->6)>-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