2-(trimethylsilyl)ethyl β-D-galactopyranosyl-(1->3)-[β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)]-2-acetamido-2-deoxy-α-D-galactopyranoside | 1163124-53-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl β-D-galactopyranosyl-(1->3)-[β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)]-2-acetamido-2-deoxy-α-D-galactopyranoside
• 英文别名: Gal(b1-4)GlcNAc(b1-6)[Gal(b1-3)]GalNAc(a)-O-EtTMS；N-[(2R,3R,4R,5S,6R)-2-[[(2R,3R,4R,5R,6S)-5-acetamido-3-hydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(2-trimethylsilylethoxy)oxan-2-yl]methoxy]-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 1163124-53-5
• 化学式: C₃₃H₆₀N₂O₂₁Si
• 分子量: 848.926
• InChiKey: LZOUGNUQBXMILI-OFTLWYBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.1
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  355
• 氢给体数：
  13
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-acetamido-6-O-acetyl-3-O-benzoyl-2-deoxy-β-D-glucopyranosyl-(1->6)]-2-acetamido-4-O-acetyl-2-deoxy-α-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以97%的产率得到2-(trimethylsilyl)ethyl β-D-galactopyranosyl-(1->3)-[β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)]-2-acetamido-2-deoxy-α-D-galactopyranoside
  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