3-O-allyl-2,4,6-tri-O-benzyl-D-mannopyranosyl trichloroacetimidate | 1046460-93-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-allyl-2,4,6-tri-O-benzyl-D-mannopyranosyl trichloroacetimidate
• CAS: 1046460-93-8
• 化学式: C₃₂H₃₄Cl₃NO₆
• 分子量: 634.984
• InChiKey: CGVTWMJEQQCJCV-AKJGHFGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.03
• 重原子数：
  42.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  79.23
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 2,4,6-tri-O-benzyl-α-D-mannopyranoside 、 3-O-allyl-2,4,6-tri-O-benzyl-D-mannopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以74%的产率得到p-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of 8-azidooctyl glycoside derivatives of the O-chain repeating unit of Escherichia coli O9a lipopolysaccharide and a methylated analog

  摘要：

  Described is the synthesis of 8-azidooctyl glycoside derivatives of the Escherichia coli serotype O9a O-chain tetrasaccharide repeating unit and the terminal tetrasaccharide motif in this polysaccharide, which contains a methyl group on O-3 of the distal mannopyranose residue. The assembly of these compounds involved the sequential addition of monosaccharide residues from the reducing to the nonreducing end of the molecule using glycosyl trichloroacetimidate donors. Both compounds were initially prepared as p-methoxyphenyl glycosides, which were converted to the corresponding 8-azidooctyl derivatives at a late stage in the synthesis. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.02.025
• 作为产物：
  描述：

  3-O-allyl-2,4,6-tri-O-benzyl-D-mannopyranoside 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到3-O-allyl-2,4,6-tri-O-benzyl-D-mannopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of 8-azidooctyl glycoside derivatives of the O-chain repeating unit of Escherichia coli O9a lipopolysaccharide and a methylated analog

  摘要：

  Described is the synthesis of 8-azidooctyl glycoside derivatives of the Escherichia coli serotype O9a O-chain tetrasaccharide repeating unit and the terminal tetrasaccharide motif in this polysaccharide, which contains a methyl group on O-3 of the distal mannopyranose residue. The assembly of these compounds involved the sequential addition of monosaccharide residues from the reducing to the nonreducing end of the molecule using glycosyl trichloroacetimidate donors. Both compounds were initially prepared as p-methoxyphenyl glycosides, which were converted to the corresponding 8-azidooctyl derivatives at a late stage in the synthesis. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.02.025