2,6-dimethylphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside | 1163124-29-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-dimethylphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside
• CAS: 1163124-29-5
• 化学式: C₄₅H₅₀Cl₃NO₁₆S
• 分子量: 999.314
• InChiKey: CFXFZRLIAVHIAL-KPNUIKIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  66.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  206.75
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  2,6-dimethylphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside 、 5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->3)-2-azido-4-O-benzyl-2-deoxy-α-D-galactopyranoside 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100%的产率得到5-(methoxycarbonyl)pentyl-2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->3)-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl-(1->6)]-2-azido-4-O-benzyl-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of the carbohydrate moiety from the parasite Echinococcus multilocularis and their antigenicity against human sera

  摘要：

  Stereocontrolled syntheses of biotin-labeled oligosaccharide portions with a Gal beta 1-3GalNAc core of the Em2 glycoprotein antigen obtained from the parasite Echinococcus multilocularis have been accomplished. Trisaccharide Gal beta 1-3(GlcNAc beta 1-6)GalNAc alpha 1-R (G), tetrasaccharide Gal beta 1-3(Gal beta 1-4GlcNAc beta 1-6)GalNAc alpha 1-R (I) and pentasaccharide Gal beta 1-3(Gal alpha 1-4Gal beta 1-4GlcNAc beta 1-6)GalNAc alpha 1-R (K) (R = biotinylated probe) were synthesized by block synthesis by the use of 5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl-(1 -> 3)-2-azido-4-O-benzyl-2-deoxy-alpha-D-galactopyranoside as a common glycosyl acceptor. Moreover, linear trisaccharide Gal alpha 1-4Gal beta 1-3GalNAc alpha 1-R (H) and branched tetrasaccharide Gal alpha 1-4Gal beta 1-3(GlcNAc beta 1-6)GalNAc alpha 1-R (1) were synthesized by stepwise wise condensation. We examined the antigenicity of these five oligosaccharides by an enzyme linked immunosorbent assay (ELISA). Our results demonstrate that biotinylated oligosaccharides H, I and K show good serodiagnostic potential to detect infections caused by the parasite E. multilocularis. Among them the linear sequence Gal alpha 1-4Gal beta 1-3GalNAc alpha 1-R in oligosaccharide (H) appears to show the highest sensitivity (95%). Moreover, our study clarified the dominant carbohydrate epitope of Em2 antigen. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.030
• 作为产物：
  描述：

  2,6-dimethylphenyl 3-O-benzoyl-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside 、 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl 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86%的产率得到2,6-dimethylphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic studies on the carbohydrate moiety of the antigen from the parasite Echinococcusmultilocularis

  摘要：

  Stereocontrolled syntheses of branched tri-, tetra-, and pentasaccharides displaying a Gal beta 1 -> 3GalNAc core in the glycan portion of the glycoprotein antigen from the parasite Echinococcus multilocularis have been accomplished. Trisaccharide Gal beta 1 -> 3(GlcNAc beta 1 -> 6)GalNAc alpha 1-OR (A). tetrasaccharide Gal beta 1 -> 3(Gal beta 1 -> 4Gal beta 1 -> 6)GalNac alpha 1-OR(D), and pentasaccharides Gal beta 1 -> 3(Gal beta 1 -> 4Gal beta 1 -> 4Gl cNAc beta 1-6)GalNAc alpha 1-OR (E) and Gal beta 1-3(Gal alpha 1 -> 4Gal alpha 1 -> 4Gal alpha 1 -> 6)GalNAc alpha 1-OR) (F) (R = 2(trimethylsilyl)ethyl) were synthesized by block synthesis. The disaccharide 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-P-D-galactopyranosyl-(1 -> 3)-2-azido-4-O-benzyl-2-deoxy-alpha-D-galactopyranoside served as a common glycosyl acceptor in the synthesis of the branched oligosaccharicles. Moreover, linear trisaccharide Gal beta 1 -> Gal beta 1 -> 3GalNac alpha 1-OR (B) and branched tetrasaccharide Gal beta 1 -> Gal beta 1 -> 3(GalNac beta 1 -> 6)GalNac alpha 1-OR (C) were synthesized by stepwise condensation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.02.019