5-(methoxycarbonyl)pentyl 4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4-O-benzyl-2-deoxy-α-D-galactopyranoside | 1296782-20-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-(methoxycarbonyl)pentyl 4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4-O-benzyl-2-deoxy-α-D-galactopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-5-[(2R,3R,4S,5S,6R)-5-acetyloxy-6-(acetyloxymethyl)-3,4-bis(phenylmethoxy)oxan-2-yl]oxy-2-[(2R,3R,4R,5R,6S)-5-azido-2-(hydroxymethyl)-6-(6-methoxy-6-oxohexoxy)-3-phenylmethoxyoxan-4-yl]oxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl] benzoate
• CAS: 1296782-20-1
• 化学式: C₇₁H₈₁N₃O₂₀
• 分子量: 1296.43
• InChiKey: RISKPRIIRLBJQH-WCUWZHOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  94
• 可旋转键数：
  38
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  241
• 氢给体数：
  1
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  5-(methoxycarbonyl)pentyl 4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4-O-benzyl-2-deoxy-α-D-galactopyranoside 、 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl 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93%的产率得到5-(methoxycarbonyl)pentyl 4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranosyl-(1->3)-[3,4,6-tri-O-acetyl-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：

  5-(methoxycarbonyl)pentyl 4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside 在 三乙基硅烷 、 二氯苯酚溴酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以85%的产率得到5-(methoxycarbonyl)pentyl 4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranosyl-(1->3)-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