10-azidodecyl O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranoside | 860036-14-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 10-azidodecyl O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranoside
• CAS: 860036-14-2
• 化学式: C₃₆H₅₅N₃O₁₈
• 分子量: 817.842
• InChiKey: CWFWYQMALAANFQ-NJXRGNBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  57.0
• 可旋转键数：
  23.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  269.78
• 氢给体数：
  0.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  10-azidodecyl O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranoside 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以91%的产率得到Acetic acid (2R,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-2-(10-amino-decyloxy)-5-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of polyanionic glycopolymers for the facile assembly of glycosyl arrays

  摘要：

  Polyanionic glycopolymers were synthesized aiming at establishing a simple process for assembling glycosyl arrays. The synthetic glycopolymers carry the key carbohydrate epitopes of alpha-D-galactobioside (Gb(2)), beta-lactoside, and U-D-mannopyranoside, each of which serves as a ligand of bacterial toxins and adhesion proteins. The Gb(2) epitope, prepared from penta-O-acetyl-D-galactopyranose, was coupled with poly(ethylene-alt-maleic anhydride) in a polymer reaction to afford a Gb(2)-embedded glycopolymer having also carboxylate (COO-) polyanions at the side chain. The polyanionic glycopolymer was then applied to a preparation of sugar-coated gold electrodes, which involves an alternating layer-by-layer adsorption based on electrostatic interactions. The presence of the Gb(2)-Coat on the surface was evidenced by Fourier transform infrared reflection absorption spectroscopy. The Gb(2)-coated glyco-chip was stable in 10 mM HEPES buffer containing 150 mM NaCl aq. Other glycopolymers carrying the beta-lactoside and alpha-D-mannopyranoside epitopes were applied to the same assembling process. The derived glycosyl arrays will be useful for detecting Shiga toxins, other pathogenic toxins and viruses when applied as glyco-chips for surface plasmon resonance or quartz crystal microbalance technique. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.102
• 作为产物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate 在 sodium azide 、 4 A molecular sieve 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 10-azidodecyl O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of polyanionic glycopolymers for the facile assembly of glycosyl arrays

  摘要：

  Polyanionic glycopolymers were synthesized aiming at establishing a simple process for assembling glycosyl arrays. The synthetic glycopolymers carry the key carbohydrate epitopes of alpha-D-galactobioside (Gb(2)), beta-lactoside, and U-D-mannopyranoside, each of which serves as a ligand of bacterial toxins and adhesion proteins. The Gb(2) epitope, prepared from penta-O-acetyl-D-galactopyranose, was coupled with poly(ethylene-alt-maleic anhydride) in a polymer reaction to afford a Gb(2)-embedded glycopolymer having also carboxylate (COO-) polyanions at the side chain. The polyanionic glycopolymer was then applied to a preparation of sugar-coated gold electrodes, which involves an alternating layer-by-layer adsorption based on electrostatic interactions. The presence of the Gb(2)-Coat on the surface was evidenced by Fourier transform infrared reflection absorption spectroscopy. The Gb(2)-coated glyco-chip was stable in 10 mM HEPES buffer containing 150 mM NaCl aq. Other glycopolymers carrying the beta-lactoside and alpha-D-mannopyranoside epitopes were applied to the same assembling process. The derived glycosyl arrays will be useful for detecting Shiga toxins, other pathogenic toxins and viruses when applied as glyco-chips for surface plasmon resonance or quartz crystal microbalance technique. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.102