methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranoside | 913174-08-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS: 913174-08-0
• 化学式: C₄₄H₅₉NO₂₃
• 分子量: 969.945
• InChiKey: WWOJSLOYZWPIFC-CRLYGZHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.73
• 重原子数：
  68.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  286.09
• 氢给体数：
  0.0
• 氢受体数：
  23.0

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-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranoside 在 sodium 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以84%的产率得到methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(β-D-glucopyranosyl)-4-O-(α-L-rhamnopyranosyl)-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：

  methyl 2-acetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 盐酸 、 三乙基硅基三氟甲磺酸酯 、 sodium cyanoborohydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzyl-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