8-azidooctyl 3-O-methyl-α-D-mannopyranosyl-(1->2)-α-D-mannopyranosyl-(1->3)-α-D-mannopyranosyl-(1->3)-α-D-mannopyranoside | 1046460-86-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-azidooctyl 3-O-methyl-α-D-mannopyranosyl-(1->2)-α-D-mannopyranosyl-(1->3)-α-D-mannopyranosyl-(1->3)-α-D-mannopyranoside
• 英文别名: (2R,3S,4S,5S,6R)-6-[(2R,3S,4S,5R,6R)-2-[(2S,3S,4S,5R,6R)-2-(8-azidooctoxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-5-[(2R,3S,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy-2-(hydroxymethyl)oxane-3,4-diol
• CAS: 1046460-86-9
• 化学式: C₃₃H₅₉N₃O₂₁
• 分子量: 833.839
• InChiKey: MAPYRXPYGXKSPO-ZMQAXHQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  57
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  340
• 氢给体数：
  12
• 氢受体数：
  23

反应信息

• 作为产物：
  描述：

  8-azidooctyl 2,4,6-tri-O-benzoyl-3-O-methyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 以83%的产率得到8-azidooctyl 3-O-methyl-α-D-mannopyranosyl-(1->2)-α-D-mannopyranosyl-(1->3)-α-D-mannopyranosyl-(1->3)-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

文献信息

• Synthesis of 8-azidooctyl glycoside derivatives of the O-chain repeating unit of Escherichia coli O9a lipopolysaccharide and a methylated analog
  作者：Dianjie Hou、Fredrik Skogman、Todd L. Lowary

  DOI：10.1016/j.carres.2008.02.025

  日期：2008.7

  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.