1L-O⁵-(O⁵-acetyl-O²,O³-cyclohexane-1,1-diyl-β-D-ribofuranosyl)-N¹-benzyloxycarbonyl-O⁶-(2,6-bis-benzyloxycarbonylamino-α-D-ribo-2,3,6-trideoxy-hexopyranosyl)-N³,O⁴-carbonyl-2-deoxy-streptamine | 57052-26-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1L-O⁵-(O⁵-acetyl-O²,O³-cyclohexane-1,1-diyl-β-D-ribofuranosyl)-N¹-benzyloxycarbonyl-O⁶-(2,6-bis-benzyloxycarbonylamino-α-D-ribo-2,3,6-trideoxy-hexopyranosyl)-N³,O⁴-carbonyl-2-deoxy-streptamine
• 英文别名: [(3aR,4S,6R,6aR)-4-[[(3aR,5S,6R,7S,7aS)-6-[(2R,3R,5S,6R)-5-hydroxy-3-(phenylmethoxycarbonylamino)-6-(phenylmethoxycarbonylaminomethyl)oxan-2-yl]oxy-2-oxo-5-(phenylmethoxycarbonylamino)-3a,4,5,6,7,7a-hexahydro-3H-1,3-benzoxazol-7-yl]oxy]spiro[3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-2,1'-cyclohexane]-6-yl]methyl acetate
• CAS: 57052-26-3
• 化学式: C₅₀H₆₀N₄O₁₇
• 分子量: 989.043
• InChiKey: LBGDUXJRBDUIIU-JIGALHNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  71
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  255
• 氢给体数：
  5
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  1L-O⁵-(O⁵-acetyl-O²,O³-cyclohexane-1,1-diyl-β-D-ribofuranosyl)-N¹-benzyloxycarbonyl-O⁶-(2,6-bis-benzyloxycarbonylamino-α-D-ribo-2,3,6-trideoxy-hexopyranosyl)-N³,O⁴-carbonyl-2-deoxy-streptamine 、 (2S)-2-(2,5-dioxopyrrolidin-1-yl)oxy-4-(phenylmethoxycarbonylamino)butanoic acid 生成 [(3aR,4S,6R,6aR)-4-[(1R,2R,3S,6S)-6-hydroxy-4-[[(2S)-2-hydroxy-4-(phenylmethoxycarbonylamino)butanoyl]amino]-2-[(2R,3R,5S,6R)-5-hydroxy-3-(phenylmethoxycarbonylamino)-6-(phenylmethoxycarbonylaminomethyl)oxan-2-yl]oxy-3-(phenylmethoxycarbonylamino)cyclohexyl]oxyspiro[3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-2,1'-cyclohexane]-6-yl]methyl acetate
  参考文献：
  名称：

  UMEHDZAVA, XAMAO;UMEHDZAVA, SUMIO;TSUTIYA, OSAMU

  摘要：

  DOI：
• 作为产物：
  描述：

  1L-O⁵-(O⁵-acetyl-O²,O³-cyclohexane-1,1-diyl-β-D-ribofuranosyl)-N¹-benzyloxycarbonyl-O⁶-(2,6-bis-benzyloxycarbonylamino-3-iodo-α-D-2,3,6-trideoxy-glucopyranosyl)-N³,O⁴-carbonyl-2-deoxy-streptamine 在 镍 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 1L-O⁵-(O⁵-acetyl-O²,O³-cyclohexane-1,1-diyl-β-D-ribofuranosyl)-N¹-benzyloxycarbonyl-O⁶-(2,6-bis-benzyloxycarbonylamino-α-D-ribo-2,3,6-trideoxy-hexopyranosyl)-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