(1S,2S,3R,4R,5S,6R)-5-amino-2-[N-(benzyloxycarbonyl)amino]-5-N,6-O-carbonyl-3,4-cyclohexylidene-1,3,4,6-cyclohexanetetrol | 179094-15-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S,3R,4R,5S,6R)-5-amino-2-[N-(benzyloxycarbonyl)amino]-5-N,6-O-carbonyl-3,4-cyclohexylidene-1,3,4,6-cyclohexanetetrol
• CAS: 179094-15-6
• 化学式: C₂₁H₂₆N₂O₇
• 分子量: 418.447
• InChiKey: ZRKYXONIAVJEOQ-SJUNHDGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  115.35
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 (1S,2S,3R,4R,5S,6R)-5-amino-2-[N-(benzyloxycarbonyl)amino]-5-N,6-O-carbonyl-3,4-cyclohexylidene-1,3,4,6-cyclohexanetetrol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以83%的产率得到(1S,2S,3R,4R,5S,6R)-5-amino-2-[N-(benzyloxycarbonyl)amino]-5-N,6-O-carbonyl-3,4-cyclohexylidene-1-O,5-N-dibenzoyl-1,3,4,6-cyclohexanetetrol
  参考文献：
  名称：

  Synthesis of 1,4-Diaminocyclitols From l-Serine Methyl Ester

  摘要：

  L-Serine methyl ester hydrochloride was converted to (S)-2-[N-(benzyloxycarbonyl)amino]-3-(tert-butyldimethylsiloxy)propanal (6). Homocoupling of 6 promoted by [V2Cl3(THF)(6)](2)[Zn2Cl6] (1) gave C-2-symmetric diol (7). After manipulation of protecting groups and Swern oxidation, 7 was converted to a 1,6-dialdehyde 10. Intramolecular pinacol coupling of 10 with 1 gave a selectively protected 1,4-diamino-2,3,5,6-tetrahydroxycyclohexane, which is the key skeleton of Fortimicin AM and AK.

  DOI：

  10.1021/jo960691a
• 作为产物：
  描述：

  (1S,2S,3R,4R,5S,6R)-2,5-bis[N-(benzyloxycarbonyl)amino]-3,4-cyclohexylidene-1,3,4,6-cyclohexanetetrol 在 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以51%的产率得到(1S,2S,3R,4R,5S,6R)-5-amino-2-[N-(benzyloxycarbonyl)amino]-5-N,6-O-carbonyl-3,4-cyclohexylidene-1,3,4,6-cyclohexanetetrol
  参考文献：
  名称：

  Synthesis of 1,4-Diaminocyclitols From l-Serine Methyl Ester

  摘要：

  L-Serine methyl ester hydrochloride was converted to (S)-2-[N-(benzyloxycarbonyl)amino]-3-(tert-butyldimethylsiloxy)propanal (6). Homocoupling of 6 promoted by [V2Cl3(THF)(6)](2)[Zn2Cl6] (1) gave C-2-symmetric diol (7). After manipulation of protecting groups and Swern oxidation, 7 was converted to a 1,6-dialdehyde 10. Intramolecular pinacol coupling of 10 with 1 gave a selectively protected 1,4-diamino-2,3,5,6-tetrahydroxycyclohexane, which is the key skeleton of Fortimicin AM and AK.

  DOI：

  10.1021/jo960691a