p-tolyl 2-acetamido-4,6-O-benzylidene-2-N,3-O-carbonyl-2-deoxy-1-thio-β-D-glucopyranoside | 905266-78-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: p-tolyl 2-acetamido-4,6-O-benzylidene-2-N,3-O-carbonyl-2-deoxy-1-thio-β-D-glucopyranoside
• CAS: 905266-78-6
• 化学式: C₂₃H₂₃NO₆S
• 分子量: 441.505
• InChiKey: GAWYEMDAWLQIJW-ILHTXMRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  p-tolyl 2-acetamido-4,6-O-benzylidene-2-N,3-O-carbonyl-2-deoxy-1-thio-β-D-glucopyranoside 在 盐酸 、 4-甲基苯硫氯 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 3.75h， 生成 p-tolyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  Iterative one-pot syntheses of chitotetroses

  摘要：

  Rapid syntheses of chitotetrose derivatives were achieved in good yields using the newly developed reactivity independent iterative one-pot strategy. The protective groups on donors and acceptors were independently evaluated allowing matching of the two partners in glycosylation. No anomeric reactivity adjustments or intermediate purification were necessary thus significantly improving the overall synthetic efficiency. Only near stoichiometric amounts of building blocks were required for the assembly of target molecules further highlighting the potential of the iterative one-pot method in complex oligosaccharide synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.01.007
• 作为产物：
  描述：

  p-methylphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 乙二胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 25.0h， 生成 p-tolyl 2-acetamido-4,6-O-benzylidene-2-N,3-O-carbonyl-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Iterative one-pot syntheses of chitotetroses

  摘要：

  Rapid syntheses of chitotetrose derivatives were achieved in good yields using the newly developed reactivity independent iterative one-pot strategy. The protective groups on donors and acceptors were independently evaluated allowing matching of the two partners in glycosylation. No anomeric reactivity adjustments or intermediate purification were necessary thus significantly improving the overall synthetic efficiency. Only near stoichiometric amounts of building blocks were required for the assembly of target molecules further highlighting the potential of the iterative one-pot method in complex oligosaccharide synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.01.007