1L-N¹-benzyloxycarbonyl-O⁶-(2,6-bis-benzyloxycarbonylamino-O³,O⁴-cyclohexane-1,1-diyl-α-D-2,6-dideoxy-glucopyranosyl)-N³,O⁴-carbonyl-O⁵-(O²,O³-cyclohexane-1,1-diyl-β-D-ribofuranosyl)-2-deoxy-streptamine | 57105-92-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 1L-N¹-benzyloxycarbonyl-O⁶-(2,6-bis-benzyloxycarbonylamino-O³,O⁴-cyclohexane-1,1-diyl-α-D-2,6-dideoxy-glucopyranosyl)-N³,O⁴-carbonyl-O⁵-(O²,O³-cyclohexane-1,1-diyl-β-D-ribofuranosyl)-2-deoxy-streptamine
• 英文别名: benzyl N-[(3aR,4R,6R,7R,7aR)-6-[[(3aR,5S,6R,7S,7aS)-7-[(3aR,4S,6R,6aR)-6-(hydroxymethyl)spiro[3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-2,1'-cyclohexane]-4-yl]oxy-2-oxo-5-(phenylmethoxycarbonylamino)-3a,4,5,6,7,7a-hexahydro-3H-1,3-benzoxazol-6-yl]oxy]-4-(phenylmethoxycarbonylaminomethyl)spiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2,1'-cyclohexane]-7-yl]carbamate
• CAS: 57105-92-7
• 化学式: C₅₄H₆₆N₄O₁₇
• 分子量: 1043.13
• InChiKey: TYXSRVQWJSDGMD-WSHKEPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  75
• 可旋转键数：
  18
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  247
• 氢给体数：
  5
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  1L-N¹-benzyloxycarbonyl-O⁶-(2,6-bis-benzyloxycarbonylamino-O³,O⁴-cyclohexane-1,1-diyl-α-D-2,6-dideoxy-glucopyranosyl)-N³,O⁴-carbonyl-O⁵-(O²,O³-cyclohexane-1,1-diyl-β-D-ribofuranosyl)-2-deoxy-streptamine 、 乙酸酐 在 吡啶 作用下， 生成 1L-O⁵-(O⁵-acetyl-O²,O³-cyclohexane-1,1-diyl-β-D-ribofuranosyl)-N¹-benzyloxycarbonyl-O⁶-(2,6-bis-benzyloxycarbonylamino-O³,O⁴-cyclohexane-1,1-diyl-α-D-2,6-dideoxy-glucopyranosyl)-N³,O⁴-carbonyl-2-deoxy-streptamine
  参考文献：
  名称：

  Synthesis of 1-N-[(S)-4-amino-2-hydroxybutyryl]-3′-deoxyribostamycin (3′-Deoxybutirosin B)

  摘要：

  3′-Deoxybutirosin B (13) was prepared from ribostamycin by way of the following reaction sequences: 1) selective 3′-O-arylsulfonylation, 3′-iodination, and 3′-deoxygenation; 2) 1,6-cyclic carbamate formation,selective hydrolysis of the carbamate and acylation of the free 1-NH2 group with an active ester of (S)-4-amino-2-hydroxybutyric acid. The structure of 13 was confirmed by comparison of its Δ[M]TACu value with those of butirosin B and 4′-deoxybutirosin B.

  DOI：

  10.1246/bcsj.49.3666
• 作为产物：
  描述：

  1D-N,N'-bis-benzyloxycarbonyl-O⁴-(2,6-bis-benzyloxycarbonylamino-O³,O⁴-cyclohexane-1,1-diyl-α-D-2,6-dideoxy-glucopyranosyl)-O⁵-(O²,O³-cyclohexane-1,1-diyl-β-D-ribofuranosyl)-2-deoxy-streptamine 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1L-N¹-benzyloxycarbonyl-O⁶-(2,6-bis-benzyloxycarbonylamino-O³,O⁴-cyclohexane-1,1-diyl-α-D-2,6-dideoxy-glucopyranosyl)-N³,O⁴-carbonyl-O⁵-(O²,O³-cyclohexane-1,1-diyl-β-D-ribofuranosyl)-2-deoxy-streptamine
  参考文献：
  名称：

  Synthesis of 1-N-[(S)-4-amino-2-hydroxybutyryl]-3′-deoxyribostamycin (3′-Deoxybutirosin B)

  摘要：

  3′-Deoxybutirosin B (13) was prepared from ribostamycin by way of the following reaction sequences: 1) selective 3′-O-arylsulfonylation, 3′-iodination, and 3′-deoxygenation; 2) 1,6-cyclic carbamate formation,selective hydrolysis of the carbamate and acylation of the free 1-NH2 group with an active ester of (S)-4-amino-2-hydroxybutyric acid. The structure of 13 was confirmed by comparison of its Δ[M]TACu value with those of butirosin B and 4′-deoxybutirosin B.

  DOI：

  10.1246/bcsj.49.3666