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-deoxy-2-trichloroacetamido-β-D-glucopyranoside | 934746-03-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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-deoxy-2-trichloroacetamido-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-6-[(2R,3S,4R,5R,6S)-6-[tert-butyl(dimethyl)silyl]oxy-4-phenylmethoxy-2-(phenylmethoxymethyl)-5-[(2,2,2-trichloroacetyl)amino]oxan-3-yl]oxy-4-phenylmethoxy-5-(phenylmethoxycarbonylamino)-2-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 934746-03-9
• 化学式: C₅₈H₆₉Cl₃N₂O₁₃Si
• 分子量: 1136.64
• InChiKey: WGNPTRPVCYFSOH-LRMLINOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.53
• 重原子数：
  77
• 可旋转键数：
  26
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  168
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  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-deoxy-2-trichloroacetamido-β-D-glucopyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 3.0h， 以75%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)-2-acetamido-3,6-di-O-benzyl-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：

  4-O-acetyl-3,6-di-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-1-O-trichloroacetimidoyl-α-D-glucopyranose 、 tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside 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-deoxy-2-trichloroacetamido-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