4-O-acetyl-3,6-di-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-1-O-trichloroacetimidoyl-α-D-glucopyranose | 1242094-98-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-acetyl-3,6-di-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-1-O-trichloroacetimidoyl-α-D-glucopyranose
• 英文别名: CbzNH(-2d)[Bn(-3)][Bn(-6)]Glc4Ac(a)-O-C(NH)CCl3；[(2R,3S,4R,5R,6R)-4-phenylmethoxy-5-(phenylmethoxycarbonylamino)-2-(phenylmethoxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] acetate
• CAS: 1242094-98-9
• 化学式: C₃₂H₃₃Cl₃N₂O₈
• 分子量: 679.982
• InChiKey: CKGVUAGISAVVSZ-HWVUQVAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyldimethylsilyl 3,6-di-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-β-D-glucopyranoside 、 4-O-acetyl-3,6-di-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-1-O-trichloroacetimidoyl-α-D-glucopyranose 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以70%的产率得到tert-butyldimethylsilyl 4-O-acetyl-3,6-di-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Towards a modular synthesis of well-defined chitooligosaccharides: synthesis of the four chitodisaccharides

  摘要：

  The total chemical synthesis of the four well-defined chitodisaccharides is described using N-trichloroacetyl (TCA) and N-benzyloxycarbonyl (Z) as C-2 protecting groups for acetamido and free amino groups, respectively. The synthesis is carried out according to a strategy that paves way to the elaboration of various homo- and hetero-chitooligosaccharides, with perfect control of the number and the position of GIcN and GIcNAc units along the oligomer chain. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.05.010
• 作为产物：
  描述：

  、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以1.9 g的产率得到4-O-acetyl-3,6-di-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-1-O-trichloroacetimidoyl-α-D-glucopyranose
  参考文献：
  名称：

  Towards a modular synthesis of well-defined chitooligosaccharides: synthesis of the four chitodisaccharides

  摘要：

  The total chemical synthesis of the four well-defined chitodisaccharides is described using N-trichloroacetyl (TCA) and N-benzyloxycarbonyl (Z) as C-2 protecting groups for acetamido and free amino groups, respectively. The synthesis is carried out according to a strategy that paves way to the elaboration of various homo- and hetero-chitooligosaccharides, with perfect control of the number and the position of GIcN and GIcNAc units along the oligomer chain. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.05.010