N,N'-((1S,3R,4R,5R,6R)-4-((tert-butyldimethylsilyl)oxy)-5,6-dihydroxycyclohexane-1,3-diyl)bis(N-benzyl-2-nitrobenzenesulfonamide) | 688334-52-3

• 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: N,N'-((1S,3R,4R,5R,6R)-4-((tert-butyldimethylsilyl)oxy)-5,6-dihydroxycyclohexane-1,3-diyl)bis(N-benzyl-2-nitrobenzenesulfonamide)
• CAS: 688334-52-3
• 化学式: C₃₈H₄₆N₄O₁₁S₂Si
• 分子量: 827.021
• InChiKey: UOTDLUWAURCFHU-WRTCRQPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.84
• 重原子数：
  56.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  210.73
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N,N'-((1S,3R,4R,5R,6R)-4-((tert-butyldimethylsilyl)oxy)-5,6-dihydroxycyclohexane-1,3-diyl)bis(N-benzyl-2-nitrobenzenesulfonamide) 在 对甲苯磺酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 Acetic acid (1R,2R,3R,5S,6R)-3,5-bis-[benzyl-(2-nitro-benzenesulfonyl)-amino]-2-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-cyclohexyl ester
  参考文献：
  名称：

  Synthesis of orthogonally protected 2-deoxystreptamine stereoisomers

  摘要：

  Enantiomerically pure 4,6-diaminocyclohexenols are obtained from carbohydrate derived 1,7-dienes by ring-closing metathesis and palladium catalyzed allylic amination using o-nitrobenzenesulfonylamides as nucleophiles. In the latter reaction the use of a cyclic carbonate as a leaving group proved to be essential to facilitate a smooth substitution. The obtained compounds were converted into orthogonally protected diaminocyclitols, which are stereoisomers of the naturally occurring 2-deoxystreptamine, a constituent of aminoglycoside antibiotics. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.063
• 作为产物：
  描述：

  (1R,2S,6R)-6-(N-benzyl)-o-nitrobenzenesulfonamino-1,2-di-O-carbonyl-cyclohex-3-ene-1,2-diol 在 吡啶 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 potassium osmate(VI) 、 N-甲基吗啉氧化物 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 79.5h， 生成 N,N'-((1S,3R,4R,5R,6R)-4-((tert-butyldimethylsilyl)oxy)-5,6-dihydroxycyclohexane-1,3-diyl)bis(N-benzyl-2-nitrobenzenesulfonamide)
  参考文献：
  名称：

  Synthesis of orthogonally protected 2-deoxystreptamine stereoisomers

  摘要：

  Enantiomerically pure 4,6-diaminocyclohexenols are obtained from carbohydrate derived 1,7-dienes by ring-closing metathesis and palladium catalyzed allylic amination using o-nitrobenzenesulfonylamides as nucleophiles. In the latter reaction the use of a cyclic carbonate as a leaving group proved to be essential to facilitate a smooth substitution. The obtained compounds were converted into orthogonally protected diaminocyclitols, which are stereoisomers of the naturally occurring 2-deoxystreptamine, a constituent of aminoglycoside antibiotics. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.063