6-azidohexyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 1352307-02-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-azidohexyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS: 1352307-02-8
• 化学式: C₈₂H₉₁N₃O₁₇
• 分子量: 1390.63
• InChiKey: ARMOGEKAXZJKNX-IGBZYQCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.23
• 重原子数：
  102.0
• 可旋转键数：
  37.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  213.51
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  6-azidohexyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以96.5%的产率得到6-azidohexyl 2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a Forssman antigen derivative for use in a conjugate vaccine

  摘要：

  The total chemical synthesis of a Forssman antigen analog is described. The pentasaccharide contains a functionalized tether which should facilitate future conjugation with immunogenic proteins. We found that the total synthesis can be efficiently achieved by following a convergent 2+3 strategy, and using N-Troc protected GalNAc thioglycoside as a donor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.09.015
• 作为产物：
  描述：

  p-chlorophenyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 、 6-azidohexyl 2,3,6-tri-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 以86.9%的产率得到6-azidohexyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a Forssman antigen derivative for use in a conjugate vaccine

  摘要：

  The total chemical synthesis of a Forssman antigen analog is described. The pentasaccharide contains a functionalized tether which should facilitate future conjugation with immunogenic proteins. We found that the total synthesis can be efficiently achieved by following a convergent 2+3 strategy, and using N-Troc protected GalNAc thioglycoside as a donor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.09.015