tert-butyldimethylsilyl 2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-β-D-glucopyranoside | 934746-10-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyldimethylsilyl 2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-β-D-glucopyranoside
• 英文别名: Bn(-3)[Bn(-6)]GlcNAc4Ac(b1-4)[CbzNH(-2d)][Bn(-3)][Bn(-6)]Glc(b)-O-TBDMS；[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3S,4R,5R,6S)-6-[tert-butyl(dimethyl)silyl]oxy-4-phenylmethoxy-5-(phenylmethoxycarbonylamino)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 934746-10-8
• 化学式: C₅₈H₇₂N₂O₁₃Si
• 分子量: 1033.3
• InChiKey: HZMQACJXKZXVIH-ROVUNGEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.18
• 重原子数：
  74
• 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 2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以87%的产率得到tert-butyldimethylsilyl 2-acetamido-3,6-di-O-benzyl-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：

  tert-butyldimethylsilyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-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82%的产率得到tert-butyldimethylsilyl 2-acetamido-4-O-acetyl-3,6-di-O-benzyl-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