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 | 216777-16-1

• 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)-(1-2)-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
• 英文别名: Man2Ac3Ac4Ac6Ac(a1-2)Man3Ac4Ac6Ac(a1-6)[Man2Ac3Ac4Ac6Ac(a1-3)][Bn(-2)][Bn(-4)]Man(a)-O-C(NH)CCl3；[(2R,3R,4S,5S,6S)-3,4-diacetyloxy-6-[[(2R,3R,4S,5S,6R)-3,5-bis(phenylmethoxy)-4-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methoxy]-5-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 216777-16-1
• 化学式: C₆₂H₇₆Cl₃NO₃₂
• 分子量: 1453.63
• InChiKey: JLPDRKHQTDRXLY-JDGOYKBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  98
• 可旋转键数：
  40
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  405
• 氢给体数：
  1
• 氢受体数：
  33

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl trichloroacetimidate 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