2,4-di-O-benzyl-N-benzyloxycarbonyl-6-O-tert-butyldimethylsilyl-1,5-dideoxy-1,5-imino-3-O-methyl-D-mannitol | 153094-28-1

• 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: 2,4-di-O-benzyl-N-benzyloxycarbonyl-6-O-tert-butyldimethylsilyl-1,5-dideoxy-1,5-imino-3-O-methyl-D-mannitol
• 英文别名: benzyl (2R,3R,4R,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-methoxy-3,5-bis(phenylmethoxy)piperidine-1-carboxylate
• CAS: 153094-28-1
• 化学式: C₃₅H₄₇NO₆Si
• 分子量: 605.847
• InChiKey: OKPXXFKEEJHBIV-XEXPGFJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.22
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4-di-O-benzyl-N-benzyloxycarbonyl-6-O-tert-butyldimethylsilyl-1,5-dideoxy-1,5-imino-3-O-methyl-D-mannitol 在 钯 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 96.0h， 以89%的产率得到1,5-dideoxy-1,5-imino-3-O-methyl-D-mannitol
  参考文献：
  名称：

  Synthesis of 1,5-dideoxy-3-O-(α-D-mannopyranosyl)-1,5-imino-D-mannitol and 1,5-dideoxy-3-O-(α-D-glucopyranosyl)-1,5-imino-D-mannitol: Powerful inhibitors of endomannosidase

  摘要：

  The synthesis and conformations of 3-O-methylDMJ, 3-O-(alpha-D-glucopyranosyl)-DMJ (Glcalpha1,3DMJ), and 3-O-(alpha-D-mannopyranosyl)-DMJ (Manalpha1,3DMJ) are described. Manalpha1,3DMJ and Glcalpha1,3DMJ are shown to be very powerful inhibitors of an endomannosidase. The potential use of these compounds in both probing the pathways of N-linked glycoprotein processing and in the chemotherapy of some viral diseases is discussed.

  DOI：

  10.1016/s0957-4166(00)82250-8
• 作为产物：
  描述：

  2,4-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-mannitol 在 咪唑 、 氢氧化钾 、 18-冠醚-6 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.25h， 生成 2,4-di-O-benzyl-N-benzyloxycarbonyl-6-O-tert-butyldimethylsilyl-1,5-dideoxy-1,5-imino-3-O-methyl-D-mannitol
  参考文献：
  名称：

  Synthesis of 1,5-dideoxy-3-O-(α-D-mannopyranosyl)-1,5-imino-D-mannitol and 1,5-dideoxy-3-O-(α-D-glucopyranosyl)-1,5-imino-D-mannitol: Powerful inhibitors of endomannosidase

  摘要：

  The synthesis and conformations of 3-O-methylDMJ, 3-O-(alpha-D-glucopyranosyl)-DMJ (Glcalpha1,3DMJ), and 3-O-(alpha-D-mannopyranosyl)-DMJ (Manalpha1,3DMJ) are described. Manalpha1,3DMJ and Glcalpha1,3DMJ are shown to be very powerful inhibitors of an endomannosidase. The potential use of these compounds in both probing the pathways of N-linked glycoprotein processing and in the chemotherapy of some viral diseases is discussed.

  DOI：

  10.1016/s0957-4166(00)82250-8

文献信息

• Synthesis of 1,5-dideoxy-3-O-(α-D-mannopyranosyl)-1,5-imino-D-mannitol and 1,5-dideoxy-3-O-(α-D-glucopyranosyl)-1,5-imino-D-mannitol: Powerful inhibitors of endomannosidase
  作者：Helen Ardron、Terry D. Butters、Frances M. Platt、Mark R. Wormald、Raymond A Dwek、George W.J. Fleet、Gary S. Jacob

  DOI：10.1016/s0957-4166(00)82250-8

  日期：1993.1

  The synthesis and conformations of 3-O-methylDMJ, 3-O-(alpha-D-glucopyranosyl)-DMJ (Glcalpha1,3DMJ), and 3-O-(alpha-D-mannopyranosyl)-DMJ (Manalpha1,3DMJ) are described. Manalpha1,3DMJ and Glcalpha1,3DMJ are shown to be very powerful inhibitors of an endomannosidase. The potential use of these compounds in both probing the pathways of N-linked glycoprotein processing and in the chemotherapy of some viral diseases is discussed.