O-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-(1->4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-(3,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl) phosphate | 91288-25-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-(1->4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-(3,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl) phosphate
• CAS: 91288-25-4
• 化学式: C₃₈H₅₅N₂O₂₇P
• 分子量: 1002.83
• InChiKey: BPBLIYMCXLOIJR-BKBHDEKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  68.0
• 可旋转键数：
  19.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  381.51
• 氢给体数：
  4.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-(1->4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-(3,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl) phosphate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以7 mg的产率得到
  参考文献：
  名称：

  The synthesis of a trisaccharide and a tetrasaccharide lipid intermediate. P1-dolichyl P2-[O-β-d-mannopyranosyl-(1→4)-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)- (1→4)-2-acetamido-2-deoxy-α-d-glucopyranosyl] diphosphate and P1-dolichyl P2-[O-α-d-mannopyranosyl-(1→3)-O-β-d-mannopyranosyl-(1→4)-O-(2-acetamido-2-deoxy-β-d- glucopyranosyl)-(1→4)-2-acetamido-2-deoxy-α-d-glucopyranosyl] diphosphate

  摘要：

  Synthetic benzyl O-(2,3,4,6,-tetra-O-acetyl-beta-D-mannopyranosyl)-(1-4)- (2-acetamido-3,6-di-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-(1-4)- 2-acetamido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside was converted, by catalytic hydrogenolysis of the benzyl groups, followed by treatment with acetyl chloride-hydrogen chloride and then "chloride-ion catalysis", into O-(2,3,4,6-tetra-O-acetyl- beta-D-mannopyranosyl)-(1-4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy beta- D-glucopyranosyl)- (1-4)-2-methyl-(3,6-di-O-acetyl-1,2-dideoxy-alpha-D- glucopyrano)-[2,1-d]-2-oxazoline. This compound was phosphorylated by treatment with dibenzyl phosphate under strictly anhydrous conditions to give after catalytic hydrogenolysis, a peracetyl trisaccharide phosphate. This was coupled with P1-dolichyl P2-diphenyl diphosphate to give, after O-deacetylation, P1-dolichyl P2-[O- beta-D-mannopyranosyl- (1-4)-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)- (1-4)-2-acetamido-2-deoxy-alpha-D-glucopyranosyl] diphosphate, a trisaccharide "lipid intermediate". O-(2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranosyl)-(1-3)-O-(2,4,6-tri-O- acetyl-beta-D-mannopyranosyl)-(1-4)-O-(2-acetamido-3,6-di-O-acetyl-2- deoxy-beta- D-glucopyranosyl)- (1-4)-(2-acetamido-3,6-di-O-acetyl-2-deoxy-alpha-D-glucopyranosyl) phosphate, synthesized from O-alpha-D-mannopyranosyl-(1-3)-O-beta-D- mannopyranosyl-(1-4)-2-acetamido-2-deoxy-D-glucopyranose that had been isolated from mannosidosis urine was coupled with P1-dolichyl P2-diphenyl diphosphate to give, after O-deacetylation, P1-dolichyl P2-[O-alpha-D-mannopyranosyl- (1-3)-O-beta-D-mannopyranosyl-(1-4)-O-(2-acetamido-2-deoxy-beta-D- glucopyranosyl)-(1-4)-2-acetamido-2-deoxy-alpha-D-glucopyranosyl] diphosphate, a tetrasaccharide "lipid intermediate".

  DOI：

  10.1016/0008-6215(84)85126-5
• 作为产物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-(1->4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-methyl-(3,6-di-O-acetyl-1,2-dideoxy-α-D-glucopyrano)-<2,1-d>-2-oxazoline 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 25.0 ℃ 、200.0 kPa 条件下， 反应 49.0h， 生成 O-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-(1->4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-(3,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl) phosphate
  参考文献：
  名称：

  The synthesis of a trisaccharide and a tetrasaccharide lipid intermediate. P1-dolichyl P2-[O-β-d-mannopyranosyl-(1→4)-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)- (1→4)-2-acetamido-2-deoxy-α-d-glucopyranosyl] diphosphate and P1-dolichyl P2-[O-α-d-mannopyranosyl-(1→3)-O-β-d-mannopyranosyl-(1→4)-O-(2-acetamido-2-deoxy-β-d- glucopyranosyl)-(1→4)-2-acetamido-2-deoxy-α-d-glucopyranosyl] diphosphate

  摘要：

  Synthetic benzyl O-(2,3,4,6,-tetra-O-acetyl-beta-D-mannopyranosyl)-(1-4)- (2-acetamido-3,6-di-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-(1-4)- 2-acetamido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside was converted, by catalytic hydrogenolysis of the benzyl groups, followed by treatment with acetyl chloride-hydrogen chloride and then "chloride-ion catalysis", into O-(2,3,4,6-tetra-O-acetyl- beta-D-mannopyranosyl)-(1-4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy beta- D-glucopyranosyl)- (1-4)-2-methyl-(3,6-di-O-acetyl-1,2-dideoxy-alpha-D- glucopyrano)-[2,1-d]-2-oxazoline. This compound was phosphorylated by treatment with dibenzyl phosphate under strictly anhydrous conditions to give after catalytic hydrogenolysis, a peracetyl trisaccharide phosphate. This was coupled with P1-dolichyl P2-diphenyl diphosphate to give, after O-deacetylation, P1-dolichyl P2-[O- beta-D-mannopyranosyl- (1-4)-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)- (1-4)-2-acetamido-2-deoxy-alpha-D-glucopyranosyl] diphosphate, a trisaccharide "lipid intermediate". O-(2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranosyl)-(1-3)-O-(2,4,6-tri-O- acetyl-beta-D-mannopyranosyl)-(1-4)-O-(2-acetamido-3,6-di-O-acetyl-2- deoxy-beta- D-glucopyranosyl)- (1-4)-(2-acetamido-3,6-di-O-acetyl-2-deoxy-alpha-D-glucopyranosyl) phosphate, synthesized from O-alpha-D-mannopyranosyl-(1-3)-O-beta-D- mannopyranosyl-(1-4)-2-acetamido-2-deoxy-D-glucopyranose that had been isolated from mannosidosis urine was coupled with P1-dolichyl P2-diphenyl diphosphate to give, after O-deacetylation, P1-dolichyl P2-[O-alpha-D-mannopyranosyl- (1-3)-O-beta-D-mannopyranosyl-(1-4)-O-(2-acetamido-2-deoxy-beta-D- glucopyranosyl)-(1-4)-2-acetamido-2-deoxy-alpha-D-glucopyranosyl] diphosphate, a tetrasaccharide "lipid intermediate".

  DOI：

  10.1016/0008-6215(84)85126-5