O-β-D-galactopyranosyl-(1->4)-O-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-D-mannopyranose | 73004-58-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-β-D-galactopyranosyl-(1->4)-O-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-D-mannopyranose
• 英文别名: beta-D-Galp-(1->4)-beta-D-GlcpNAc-(1->2)-alpha-D-Manp；N-[(2S,3R,4R,5S,6R)-4-hydroxy-6-(hydroxymethyl)-2-[(2S,3S,4S,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 73004-58-7
• 化学式: C₂₀H₃₅NO₁₆
• 分子量: 545.495
• InChiKey: REVOVWCTUZRTEK-IXSWIARLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.3
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  278
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 O-β-D-galactopyranosyl-(1->4)-O-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-D-mannopyranose 以 吡啶 为溶剂， 反应 12.0h， 生成 Acetic acid (2R,3S,4R,5R,6S)-2-acetoxymethyl-5-acetylamino-6-((2R,3S,4S,5R,6R)-2,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-3-yloxy)-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Chemoenzymatic synthesis of the branched oligosaccharides which correspond to the core structures of N-linked sugar chains

  摘要：

  Synthetic routes are described to a partial structure common to all high mannose-type sugar chains and complex-type sugar chains based on a chemoenzymatic strategy which incorporates, (a) enzymatic synthesis of oligosaccharide blocks using glycosidases, and (b) chemical synthesis of the branching oligosaccharides via regioselective coupling. All reaction products correspond to key intermediates necessary for the construction of N-linked oligosaccharides and we have synthesized the branched tetra-manno-oligosaccharide high mannose-type sugar chain and the branched hexa-oligosaccharide complex-type sugar chain using this simple and direct method. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)10001-5
• 作为产物：
  描述：

  2-邻苯二甲酰亚胺基乳糖胺,七乙酸酯 在 palladium on activated charcoal 吡啶 、 2,4,6-三甲基吡啶 、 氢溴酸 、 氢气 、 sodium methylate 、 silver trifluoromethanesulfonate 、 一水合肼 作用下， 以 二氯甲烷 为溶剂， 25.0 ℃ 、400.0 kPa 条件下， 反应 4.0h， 生成 O-β-D-galactopyranosyl-(1->4)-O-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-D-mannopyranose
  参考文献：
  名称：

  包含末端N-乙酰基-β-D-乳糖胺基残基的三糖，五糖和七糖的合成，糖基糖是糖蛋白的``复合型''碳水化合物部分的一部分

  摘要：

  三氟甲磺酸银促进的3,6-二-O-（2,3,4,6-四-O-乙酰基-β - D-吡喃半乳糖基）-2-脱氧-2-邻苯二甲酰亚胺-β - D-吡喃葡萄糖基溴的缩合反应用苄基3- ö -苄基-4,6- ö苄基偏二-α- d -mannopyranoside，苄基3,6-二- ö苄基α- d -mannopyranoside，和苄基3,6-二- ö -（3,4,6-三-O-苄基-α - D-甘露吡喃糖基）-2,4-二-O-苄基-α - Dβ-甘露糖吡喃糖苷分别以66％，72％和56％的收率得到了受保护的三糖，五糖和七糖衍生物。将2-脱氧-2-邻苯二甲酰亚胺基团交换成2-乙酰氨基-2-脱氧基团并解封后，获得了游离的寡糖。

  DOI：

  10.1039/p19810002070

文献信息

• Synthesis of a tri-, a penta-, and a hepta-saccharide containing terminal N-acetyl-β-<scp>D</scp>-lactosaminyl residues, part of the ‘complex-type’ carbohydrate moiety of glycoproteins
  作者：Jan Arnarp、Jörgen Lönngren

  DOI：10.1039/p19810002070

  日期：——

  Silver trifluoromethanesulphonate-promoted condensation of 3,6-di-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide with benzyl 3-O-benzyl-4,6-O-benzyl-idene-α-D-mannopyranoside, benzyl 3,6-di-O-benzyl-α-D-mannopyranoside, and benzyl 3,6-di-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranoside gave the protected tri-, penta-, and

  三氟甲磺酸银促进的3,6-二-O-（2,3,4,6-四-O-乙酰基-β - D-吡喃半乳糖基）-2-脱氧-2-邻苯二甲酰亚胺-β - D-吡喃葡萄糖基溴的缩合反应用苄基3- ö -苄基-4,6- ö苄基偏二-α- d -mannopyranoside，苄基3,6-二- ö苄基α- d -mannopyranoside，和苄基3,6-二- ö -（3,4,6-三-O-苄基-α - D-甘露吡喃糖基）-2,4-二-O-苄基-α - Dβ-甘露糖吡喃糖苷分别以66％，72％和56％的收率得到了受保护的三糖，五糖和七糖衍生物。将2-脱氧-2-邻苯二甲酰亚胺基团交换成2-乙酰氨基-2-脱氧基团并解封后，获得了游离的寡糖。
• Chemoenzymatic synthesis of the branched oligosaccharides which correspond to the core structures of N-linked sugar chains
  作者：Ichiro Matsuo、Megumi Isomura、Tatsuo Miyazaki、Tohru Sakakibara、Katsumi Ajisaka

  DOI：10.1016/s0008-6215(97)10001-5

  日期：1997.12

  Synthetic routes are described to a partial structure common to all high mannose-type sugar chains and complex-type sugar chains based on a chemoenzymatic strategy which incorporates, (a) enzymatic synthesis of oligosaccharide blocks using glycosidases, and (b) chemical synthesis of the branching oligosaccharides via regioselective coupling. All reaction products correspond to key intermediates necessary for the construction of N-linked oligosaccharides and we have synthesized the branched tetra-manno-oligosaccharide high mannose-type sugar chain and the branched hexa-oligosaccharide complex-type sugar chain using this simple and direct method. (C) 1998 Elsevier Science Ltd.