Bis-((S)-4-{(4R,5R)-5-[(1R,2R)-2-benzyloxycarbonylamino-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-hydroxy-butyl)-carbamic acid tert-butyl ester | 203449-78-9

• 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: Bis-((S)-4-{(4R,5R)-5-[(1R,2R)-2-benzyloxycarbonylamino-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-hydroxy-butyl)-carbamic acid tert-butyl ester
• CAS: 203449-78-9
• 化学式: C₆₉H₁₂₅N₃O₁₆Si₄
• 分子量: 1365.1
• InChiKey: SGVFXSBFFAAAQQ-IWLZXHNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.96
• 重原子数：
  92.0
• 可旋转键数：
  30.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  220.5
• 氢给体数：
  4.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  Bis-((S)-4-{(4R,5R)-5-[(1R,2R)-2-benzyloxycarbonylamino-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-hydroxy-butyl)-carbamic acid tert-butyl ester 在 palladium on activated charcoal 咪唑 、 氢气 、 碘 、 三苯基膦 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 生成 Bis-{3-[(3aR,4R,6R,7R,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-4-yl]-propyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Scaffolded bis-azasugars: A dual warhead approach to glycosidase inhibition

  摘要：

  Double Suzuki coupling was achieved with vinyl bromide 7, synthesized from the bromobenzene microbial oxidation metabolite bromocyclohexadienediol 6 and alpha,omega-diborane coupling partners derived from the hydroboration of the corresponding diene. Ozonolysis and selective reduction protocols served to provide selectively the aia or pip tethered polyhydroxylated piperidine ring systems (bis-azabugars). The C-8 linked DMJ analogue 1 showed inhibitory activity against glycosidase enzymes. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10616-5
• 作为产物：
  描述：

  dibenzyl ((3aR,3a'R,4R,4'R,5R,5'R,7aR,7a'R)-(((tert-butoxycarbonyl)azanediyl)bis(propane-3,1-diyl))bis(4-((tert-butyldimethylsilyl)oxy)-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxole-7,5-diyl))dicarbamate 在 咪唑 、 sodium tetrahydroborate 、 (-)-3-去氢莽草酸 、 臭氧 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Bis-((S)-4-{(4R,5R)-5-[(1R,2R)-2-benzyloxycarbonylamino-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-hydroxy-butyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Scaffolded bis-azasugars: A dual warhead approach to glycosidase inhibition

  摘要：

  Double Suzuki coupling was achieved with vinyl bromide 7, synthesized from the bromobenzene microbial oxidation metabolite bromocyclohexadienediol 6 and alpha,omega-diborane coupling partners derived from the hydroboration of the corresponding diene. Ozonolysis and selective reduction protocols served to provide selectively the aia or pip tethered polyhydroxylated piperidine ring systems (bis-azabugars). The C-8 linked DMJ analogue 1 showed inhibitory activity against glycosidase enzymes. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10616-5