phenyl O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1-3)-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside | 210295-20-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1-3)-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside
• 英文别名: Man2Ac3Ac4Ac6Ac(a1-3)[Bn(-2)][Bn(-4)]Man(a)-SPh；[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5S,6R)-2-(hydroxymethyl)-3,5-bis(phenylmethoxy)-6-phenylsulfanyloxan-4-yl]oxyoxan-2-yl]methyl acetate
• CAS: 210295-20-8
• 化学式: C₄₀H₄₆O₁₄S
• 分子量: 782.863
• InChiKey: DPVKVMXVBFMCRX-YNFJGCEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  55
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  197
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  phenyl O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1-3)-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 5.5h， 生成 O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1-2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1-6)-[O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1-3)]-2,4-di-O-benzyl-D-mannopyranosyl trichloroacetimidate
  参考文献：
  名称：

  A Short, Efficient Synthesis of the Octamannan Residue of High Mannose Type Sugar Chains

  摘要：

  An efficient route for the synthesis of octamannan 1, found in high mannose type sugar chains, is described. To construct octasaccharide 1 by as few synthetic steps as possible, we employed a chemoenzymatic strategy: the enzymatic synthesis of oligosaccharide blocks using glycosidases followed by chemical coupling to form a branched structure. By use of this methodology, many synthetic steps were eliminated and 1 was easily synthesized.

  DOI：

  10.1080/07328309808001897
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基吡喃己糖 在 三氟甲磺酸 、 AW 300 MS 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 phenyl O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1-3)-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside
  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