p-chlorophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside | 1352307-22-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: p-chlorophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside
• CAS: 1352307-22-2
• 化学式: C₃₆H₄₀Cl₄N₂O₁₄S
• 分子量: 898.597
• InChiKey: WXGHYORQRVKLLL-AQGFOTBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  57.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  192.48
• 氢给体数：
  2.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  p-chlorophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside 、 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 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， 反应 1.0h， 以88.6%的产率得到6-azidohexyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranosyl-(1->3)-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 2-acetamido-3-O-acetyl-2-deoxy-4,6-di-O-pivaloyl-1-thio-β-D-galactopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 triflic azide 、 potassium carbonate 、 copper(II) sulfate 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 22.0h， 生成 p-chlorophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside
  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