2,6-dimethylphenyl 2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranosyl-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside | 1163124-36-4

• 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-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranosyl-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside
• CAS: 1163124-36-4
• 化学式: C₅₈H₅₈Cl₃NO₁₃S
• 分子量: 1115.52
• InChiKey: UDURJOVCPXDOAU-GTIQDDICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.53
• 重原子数：
  76.0
• 可旋转键数：
  21.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  166.54
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  2,3-di-O-benzyl-4,6-di-tert-butylsilylene-α-D-galactopyranosyl fluoride 、 2,6-dimethylphenyl 2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranosyl-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside 在 Cp₂HfCl₂ 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以91%的产率得到2,6-dimethylphenyl 2,3-di-O-benzyl-4,6-di-tert-butylsilylene-α-D-galactopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-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
• 作为产物：
  描述：

  2,6-dimethylphenyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranosyl-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside 在 吡啶 、 硫脲 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以73%的产率得到2,6-dimethylphenyl 2-O-benzoyl-3,6-di-O-benzyl-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