tert-butyldimethylsilyl 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 | 934746-08-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyldimethylsilyl 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
• 英文别名: CbzNH(-2d)[Bn(-3)][Bn(-6)]Glc(b1-4)[Bn(-3)][Bn(-6)]GlcNAc(b)-O-TBDMS；benzyl N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-6-[tert-butyl(dimethyl)silyl]oxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-hydroxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]carbamate
• CAS: 934746-08-4
• 化学式: C₅₆H₇₀N₂O₁₂Si
• 分子量: 991.264
• InChiKey: DPIAVFYVXPHHOT-LRMLINOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.61
• 重原子数：
  71
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  162
• 氢给体数：
  3
• 氢受体数：
  12

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-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 在 溶剂黄146 、 tetra-n-butylammoniumfluoride trihydrate 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以89%的产率得到3,6-di-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-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
• 作为产物：
  描述：

  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 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以95%的产率得到tert-butyldimethylsilyl 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