O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-mannopyranosyl)-(1->4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-D-glucopyranose | 88155-79-7

• 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-α-D-mannopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-mannopyranosyl)-(1->4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-D-glucopyranose
• 英文别名: O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1<*>3)-O-(2,4,6-tri-O-acetyl-β-D-mannopyranosyl)-(1<*>4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-D-glucopyranose
• CAS: 88155-79-7
• 化学式: C₄₀H₅₅NO₂₆
• 分子量: 965.868
• InChiKey: VTRHBUACPZEAJF-ILPOPVNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.72
• 重原子数：
  67.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  338.25
• 氢给体数：
  1.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-mannopyranosyl)-(1->4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-D-glucopyranose 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 O-α-D-Mannopyranosyl-(1-> 3)-O-β-D-mannopyranosyl-(1-> 4)-2-acetamido-2-desoxy-β-D-glucopyranose 、 α-D-Man(1-> 3)-β-D-Man(1-> 4)-α-D-GlcNAc
  参考文献：
  名称：

  Paulsen, Hans; Lebuhn, Rolf, Liebigs Annalen der Chemie, 1983, # 6, p. 1047 - 1072

  摘要：

  DOI：
• 作为产物：
  描述：

  2-acetamido-1,6-anhydro-3-O-benzyl-2-deoxy-4-O-(3-O-allyl-2,4,6-tri-O-benzyl-β-D-mannopyranosyl)-β-D-glucopyranose 在 10% palladium on active carbon 吡啶 、 三乙烯二胺 、 calcium sulfate 、 Wilkinson's catalyst 、 三氟化硼乙醚 、 氢气 、 氰化汞 作用下， 以 硝基甲烷 、 乙醇 、 水 、 溶剂黄146 、 苯 为溶剂， 反应 150.0h， 生成 O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-mannopyranosyl)-(1->4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-D-glucopyranose
  参考文献：
  名称：

  Itoh, Yoshio; Tejima, Setsuzo, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 5, p. 1632 - 1640

  摘要：

  DOI：

文献信息

• Oligosaccharide oxazolines: Preparation, and application to the synthesis of glycoprotein carbohydrate structures
  作者：Christopher D. Warren、Roger W. Jeanloz、Gérard Strecker

  DOI：10.1016/s0008-6215(00)85984-4

  日期：——
• 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
  作者：Christopher D. Warren、Marie-Louise Milat、Claudine Augé、Roger W. Jeanloz

  DOI：10.1016/0008-6215(84)85126-5

  日期：1984.3

  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".