methyl 6-O-benzyl-2-deoxy-2-phthalimido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside | 176106-79-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-benzyl-2-deoxy-2-phthalimido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside
• CAS: 176106-79-9
• 化学式: C₄₉H₅₁NO₁₁
• 分子量: 829.944
• InChiKey: LDIXSVCITJEMGT-BGVPUOGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.49
• 重原子数：
  61.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  131.45
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide 、 methyl 6-O-benzyl-2-deoxy-2-phthalimido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside 在 2,4,6-三甲基吡啶 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 以87%的产率得到methyl 6-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactosyl)-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of mono-, di- and trisulfated Lewis x trisaccharides

  摘要：

  3'-Sulfated and 3',6'-disulfated Lewis x trisaccharides have been prepared through selective sulfation of methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-beta-D-galactopyranosyl-3-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-beta-D-glucopyranoside, followed by catalytic hydrogenolysis. In a similar manner, 3',6-disulfated and 3',6,6'-trisulfated Lewis x trisaccharides have been !;electively obtained from methyl 2-acetamido-2-deoxy-4-O-beta-D-galactopyranosyl-3-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-beta-D-glucopyranoside. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00246-8
• 作为产物：
  描述：

  ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-thio-β-D-glucopyranoside 在 盐酸 、 4 A molecular sieve 、 sodium cyanoborohydride 、 tris(p-bromophenylammoniumyl) hexachloroantimonate 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 1.33h， 生成 methyl 6-O-benzyl-2-deoxy-2-phthalimido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of mono-, di- and trisulfated Lewis x trisaccharides

  摘要：

  3'-Sulfated and 3',6'-disulfated Lewis x trisaccharides have been prepared through selective sulfation of methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-beta-D-galactopyranosyl-3-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-beta-D-glucopyranoside, followed by catalytic hydrogenolysis. In a similar manner, 3',6-disulfated and 3',6,6'-trisulfated Lewis x trisaccharides have been !;electively obtained from methyl 2-acetamido-2-deoxy-4-O-beta-D-galactopyranosyl-3-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-beta-D-glucopyranoside. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00246-8