benzyl N-[(3aR,4R,5R,7aR)-7-[8-[(3aR,6R,7R,7aR)-7-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-6-(phenylmethoxycarbonylamino)-3a,6,7,7a-tetrahydro-1,3-benzodioxol-4-yl]octyl]-4-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-5-yl]carbamate | 203449-53-0

• 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: benzyl N-[(3aR,4R,5R,7aR)-7-[8-[(3aR,6R,7R,7aR)-7-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-6-(phenylmethoxycarbonylamino)-3a,6,7,7a-tetrahydro-1,3-benzodioxol-4-yl]octyl]-4-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-5-yl]carbamate
• CAS: 203449-53-0
• 化学式: C₅₄H₈₄N₂O₁₀Si₂
• 分子量: 977.439
• InChiKey: KEOJLOUAWXINHX-ZEOVOZKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  68.0
• 可旋转键数：
  19.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  132.04
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  benzyl N-[(3aR,4R,5R,7aR)-7-[8-[(3aR,6R,7R,7aR)-7-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-6-(phenylmethoxycarbonylamino)-3a,6,7,7a-tetrahydro-1,3-benzodioxol-4-yl]octyl]-4-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-5-yl]carbamate 在 吡啶 、 咪唑 、 sodium tetrahydroborate 、 2,3-二巯基丁二酸 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Methanesulfonic acid (1S,10S)-1,10-bis-{(4S,5R)-5-[(1R,2R)-2-benzyloxycarbonylamino-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-10-methanesulfonyloxy-decyl 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：

  1,7-辛二烯 、 [(3aR,4R,5R,7aS)-7-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-carbamic acid benzyl ester 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 、 9-borabicyclo[3.3.1]nonane dimer 作用下， 生成 benzyl N-[(3aR,4R,5R,7aR)-7-[8-[(3aR,6R,7R,7aR)-7-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-6-(phenylmethoxycarbonylamino)-3a,6,7,7a-tetrahydro-1,3-benzodioxol-4-yl]octyl]-4-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-5-yl]carbamate
  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