Man2Ac3Ac4Ac6Ac(a1-2)Man3Ac4Ac6Ac(a1-6)[Bn(-2)][Bn(-4)]Man(a)-SPh | 210295-22-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Man2Ac3Ac4Ac6Ac(a1-2)Man3Ac4Ac6Ac(a1-6)[Bn(-2)][Bn(-4)]Man(a)-SPh
• 英文别名: [(2R,3R,4S,5S,6S)-3,4-diacetyloxy-6-[[(2R,3S,4S,5S,6R)-4-hydroxy-3,5-bis(phenylmethoxy)-6-phenylsulfanyloxan-2-yl]methoxy]-5-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 210295-22-0
• 化学式: C₅₂H₆₂O₂₂S
• 分子量: 1071.12
• InChiKey: ZSBRIFPWFSSPLO-IBYJVOQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  75
• 可旋转键数：
  29
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  294
• 氢给体数：
  1
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  2,3,4,6-四-O-乙酰基-α-D-吡喃甘露糖 三氯乙酰亚胺酯 、 Man2Ac3Ac4Ac6Ac(a1-2)Man3Ac4Ac6Ac(a1-6)[Bn(-2)][Bn(-4)]Man(a)-SPh 在 三氟甲磺酸 、 AW 300 MS 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以11 mg的产率得到phenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)]-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)..
  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：

  phenyl 2,4-di-O-benzyl-1-thio-α-D-mannopyranoside 、 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl trichloroacetimidate 在 三氟甲磺酸 、 AW 300 MS 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以35 mg的产率得到Man2Ac3Ac4Ac6Ac(a1-2)Man3Ac4Ac6Ac(a1-6)[Bn(-2)][Bn(-4)]Man(a)-SPh
  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