phenyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside | 181023-18-7

• 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: phenyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside
• CAS: 181023-18-7
• 化学式: C₄₁H₄₁NO₁₆S
• 分子量: 835.84
• InChiKey: OTTOEBNTPBHGPL-VLBSIEJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  59.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  216.8
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  phenyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 tris(p-bromophenylammoniumyl) hexachloroantimonate 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 1.67h， 生成 methyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-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：

  2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 三丁基氧化锡 、 tin(ll) chloride 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 22.0h， 生成 phenyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-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