2-azidoethyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-galactopyranoside | 593252-76-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azidoethyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-galactopyranoside
• 英文别名: [(2R,3R,4R,5R,6S)-5-acetamido-6-(2-azidoethoxy)-3,4-dibenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 593252-76-7
• 化学式: C₃₁H₃₀N₄O₉
• 分子量: 602.601
• InChiKey: DGUGUYNEFXLCOW-DOMIEJOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-azidoethyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-galactopyranoside 在 palladium on activated charcoal 吡啶 、 氢气 、 sodium methylate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 70.33h， 生成 Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-{2-[6-(2-bromo-acetylamino)-hexanoylamino]-ethoxy}-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Cu(II)-Self-assembling bipyridyl-glycoclusters and dendrimers bearing the Tn-antigen cancer marker: syntheses and lectin binding properties

  摘要：

  Using the carbohydrate cancer marker, T-N-antigen (alpha-GalNAc-OR), covalently linked to a bipyridine core, square planar complexes were formed by self-assembly upon simple addition of Cu(11) sulfate. The required alpha-D-GalNAc-OR building block was constructed from 2-azidoethyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside (GlcNAc) by epimerization at C-4 of a suitably protected derivative followed by conventional modifications to provide 2-aminoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-galactopyranoside. The 2-aminoethyl aglycone was further elongated into a key monomer having an aminocaproic acid spacer together with their corresponding dimers using a double N-alkylation strategy of their N-bromoacetyl derivatives using mono-Boc-1,4-diaminobutane, respectively. The building blocks containing the bipyridyl dimers, having either a short or a long spacer arm, together with the tetramer built from the short spacer derivative were prepared in a convergent manner using 2,2'-bipyridine-4,4'-dicarboxylic acid chloride and the aminated sugar derivatives, respectively. Copper(II)-nucleated GalNAc derivatives containing four and eight residues were obtained from an aqueous solution of the bipyridyl derivatives. The relative inhibitory potencies of these glycodendrimers were evaluated against monomeric allyl alpha-D-GalNAc using a solid-phase competition assay with asialoglycophorin and horseradish peroxidase-labeled lectin Vicia villosa. The di- and tetra-valent bipyridyl clusters showed up to 87-fold increased inhibitory properties (IC50 7.14, 1.82, 4.09 muM, respectively) when compared to the monomer (IC50 158.3 muM) while the Cu(II)-complexes showed up to a 259-fold increase potencies (IC50 0.61 muM) with the octamer showing the highest affinity. However, when expressed on a per-saccharide basis, the tetramer Cu(II) nucleated derivative, possessing the longest inter-sugar distances showed the highest affinity (IC50 0.63 muM). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00438-1
• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-Alpha-D-吡喃糖 在 吡啶 、 sodium azide 、 乙酰氯 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 69.0h， 生成 2-azidoethyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Cu(II)-Self-assembling bipyridyl-glycoclusters and dendrimers bearing the Tn-antigen cancer marker: syntheses and lectin binding properties

  摘要：

  Using the carbohydrate cancer marker, T-N-antigen (alpha-GalNAc-OR), covalently linked to a bipyridine core, square planar complexes were formed by self-assembly upon simple addition of Cu(11) sulfate. The required alpha-D-GalNAc-OR building block was constructed from 2-azidoethyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside (GlcNAc) by epimerization at C-4 of a suitably protected derivative followed by conventional modifications to provide 2-aminoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-galactopyranoside. The 2-aminoethyl aglycone was further elongated into a key monomer having an aminocaproic acid spacer together with their corresponding dimers using a double N-alkylation strategy of their N-bromoacetyl derivatives using mono-Boc-1,4-diaminobutane, respectively. The building blocks containing the bipyridyl dimers, having either a short or a long spacer arm, together with the tetramer built from the short spacer derivative were prepared in a convergent manner using 2,2'-bipyridine-4,4'-dicarboxylic acid chloride and the aminated sugar derivatives, respectively. Copper(II)-nucleated GalNAc derivatives containing four and eight residues were obtained from an aqueous solution of the bipyridyl derivatives. The relative inhibitory potencies of these glycodendrimers were evaluated against monomeric allyl alpha-D-GalNAc using a solid-phase competition assay with asialoglycophorin and horseradish peroxidase-labeled lectin Vicia villosa. The di- and tetra-valent bipyridyl clusters showed up to 87-fold increased inhibitory properties (IC50 7.14, 1.82, 4.09 muM, respectively) when compared to the monomer (IC50 158.3 muM) while the Cu(II)-complexes showed up to a 259-fold increase potencies (IC50 0.61 muM) with the octamer showing the highest affinity. However, when expressed on a per-saccharide basis, the tetramer Cu(II) nucleated derivative, possessing the longest inter-sugar distances showed the highest affinity (IC50 0.63 muM). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00438-1

文献信息

• Cu(II)-Self-assembling bipyridyl-glycoclusters and dendrimers bearing the Tn-antigen cancer marker: syntheses and lectin binding properties
  作者：René Roy、Jin Mi Kim

  DOI：10.1016/s0040-4020(03)00438-1

  日期：2003.5

  Using the carbohydrate cancer marker, T-N-antigen (alpha-GalNAc-OR), covalently linked to a bipyridine core, square planar complexes were formed by self-assembly upon simple addition of Cu(11) sulfate. The required alpha-D-GalNAc-OR building block was constructed from 2-azidoethyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside (GlcNAc) by epimerization at C-4 of a suitably protected derivative followed by conventional modifications to provide 2-aminoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-galactopyranoside. The 2-aminoethyl aglycone was further elongated into a key monomer having an aminocaproic acid spacer together with their corresponding dimers using a double N-alkylation strategy of their N-bromoacetyl derivatives using mono-Boc-1,4-diaminobutane, respectively. The building blocks containing the bipyridyl dimers, having either a short or a long spacer arm, together with the tetramer built from the short spacer derivative were prepared in a convergent manner using 2,2'-bipyridine-4,4'-dicarboxylic acid chloride and the aminated sugar derivatives, respectively. Copper(II)-nucleated GalNAc derivatives containing four and eight residues were obtained from an aqueous solution of the bipyridyl derivatives. The relative inhibitory potencies of these glycodendrimers were evaluated against monomeric allyl alpha-D-GalNAc using a solid-phase competition assay with asialoglycophorin and horseradish peroxidase-labeled lectin Vicia villosa. The di- and tetra-valent bipyridyl clusters showed up to 87-fold increased inhibitory properties (IC50 7.14, 1.82, 4.09 muM, respectively) when compared to the monomer (IC50 158.3 muM) while the Cu(II)-complexes showed up to a 259-fold increase potencies (IC50 0.61 muM) with the octamer showing the highest affinity. However, when expressed on a per-saccharide basis, the tetramer Cu(II) nucleated derivative, possessing the longest inter-sugar distances showed the highest affinity (IC50 0.63 muM). (C) 2003 Elsevier Science Ltd. All rights reserved.