methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside | 913174-05-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• CAS: 913174-05-7
• 化学式: C₃₂H₄₁NO₁₆
• 分子量: 695.675
• InChiKey: CVOXAVAFYNGWJO-OFRREBEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  49.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  197.96
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium 、 sodium cyanoborohydride 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 43.0h， 生成 methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl(1->3)-[α-L-fucopyranosyl-(1->4)]-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Lewis A trisaccharide analogues in which d-glucose and l-rhamnose replace d-galactose and l-fucose, respectively

  摘要：

  In our effort to design a safe anti-cancer vaccine based on the tumor associated carbohydrate antigen Le(a)Le(x), we are studying the cross-reactivity between the Le(a) natural trisaccharide antigen and analogues in which the L-fucose, D-galactose, and/or D-glucosamine residues are replaced by L-rhamnose or D-glucose, respectively. We describe here the chemical synthesis of two such Le(a) trisaccharide analogues. In one trisaccharide, D-glucose replaces D-galactose and in the second analogue L-rhamnose and D-glucose replace L-fucose and D-galactose, respectively. Introduction of the rhamnose and fucose moiety onto the poorly reactive 4-OH group of the N-acetylglucosamine residue in a disaccharide acceptor was successful after bis-N-acetylation of the amine group. These analogues will be used in competitive binding experiments with anti-Le(a) antibodies and their solution conformations will be studied. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.07.006
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 氰化汞 、 N,N-二异丙基乙胺 作用下， 以 硝基甲烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 16.0h， 生成 methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Lewis A trisaccharide analogues in which d-glucose and l-rhamnose replace d-galactose and l-fucose, respectively

  摘要：

  In our effort to design a safe anti-cancer vaccine based on the tumor associated carbohydrate antigen Le(a)Le(x), we are studying the cross-reactivity between the Le(a) natural trisaccharide antigen and analogues in which the L-fucose, D-galactose, and/or D-glucosamine residues are replaced by L-rhamnose or D-glucose, respectively. We describe here the chemical synthesis of two such Le(a) trisaccharide analogues. In one trisaccharide, D-glucose replaces D-galactose and in the second analogue L-rhamnose and D-glucose replace L-fucose and D-galactose, respectively. Introduction of the rhamnose and fucose moiety onto the poorly reactive 4-OH group of the N-acetylglucosamine residue in a disaccharide acceptor was successful after bis-N-acetylation of the amine group. These analogues will be used in competitive binding experiments with anti-Le(a) antibodies and their solution conformations will be studied. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.07.006