phenyl 3,4,6-tri-O-benzyl-2-O-<6-O-benzyl-2-deoxy-2-phthalimido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranosyl>-1-thio-α-D-mannopyranoside | 169049-01-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,4,6-tri-O-benzyl-2-O-<6-O-benzyl-2-deoxy-2-phthalimido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranosyl>-1-thio-α-D-mannopyranoside
• 英文别名: 2-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-phenylsulfanyloxan-3-yl]oxy-5-hydroxy-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione
• CAS: 169049-01-8
• 化学式: C₈₁H₈₁NO₁₅S
• 分子量: 1340.6
• InChiKey: FUBZKLSIWRPMDU-NANBWZKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  98
• 可旋转键数：
  30
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  194
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide 、 phenyl 3,4,6-tri-O-benzyl-2-O-<6-O-benzyl-2-deoxy-2-phthalimido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranosyl>-1-thio-α-D-mannopyranoside 在 2,4,6-三甲基吡啶 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 以78%的产率得到phenyl 3,4,6-tri-O-benzyl-2-O-<6-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranosyl>-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of a nonasaccharide with two lewis x trisaccharides anchored onto a branched trimannoside

  摘要：

  Double condensation of phenyl 3,4,6-tri-O-benzyl-2-O-[6-O-benzyl-2-deoxy-2-phthalimido-4-O-(2 ,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl)-3-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-beta-D-glucopyranosyl]- 1-thio-alpha-D-mannopyranoside 31 with methyl 2,4-di-O-benzyl-beta-D-mannopyranoside 35, in the presence of N-iodosuccinimide/trifluoromethane-sulfonic acid, gave the protected nonasaccharide 36 in 60% yield. Conventional deprotection gave the nonasaccharide 1, in which two Lewis x trisaccharides are anchored onto a branched trimannoside.

  DOI：

  10.1016/0957-4166(95)00146-g
• 作为产物：
  描述：

  phenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 在 三氯化铝 、 硼烷-三甲胺络合物 、 sodium methylate 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 96.0h， 生成 phenyl 3,4,6-tri-O-benzyl-2-O-<6-O-benzyl-2-deoxy-2-phthalimido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranosyl>-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of a nonasaccharide with two lewis x trisaccharides anchored onto a branched trimannoside

  摘要：

  Double condensation of phenyl 3,4,6-tri-O-benzyl-2-O-[6-O-benzyl-2-deoxy-2-phthalimido-4-O-(2 ,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl)-3-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-beta-D-glucopyranosyl]- 1-thio-alpha-D-mannopyranoside 31 with methyl 2,4-di-O-benzyl-beta-D-mannopyranoside 35, in the presence of N-iodosuccinimide/trifluoromethane-sulfonic acid, gave the protected nonasaccharide 36 in 60% yield. Conventional deprotection gave the nonasaccharide 1, in which two Lewis x trisaccharides are anchored onto a branched trimannoside.

  DOI：

  10.1016/0957-4166(95)00146-g