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 | 934746-11-9

• 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-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)]GlcNAc(b1-4)[CbzNH(-2d)][Bn(-3)][Bn(-6)]Glc(b)-O-TBDMS；benzyl N-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-hydroxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2-[tert-butyl(dimethyl)silyl]oxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]carbamate
• CAS: 934746-11-9
• 化学式: C₅₆H₇₀N₂O₁₂Si
• 分子量: 991.264
• InChiKey: RJNSELNAJFSGNF-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 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 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 48.0h， 以75%的产率得到tert-butyldimethylsilyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-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 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