tert-butyldiphenylsilyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranose

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyldiphenylsilyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranose
• 英文别名: Bn(-3)[Bn(-4)][Bn(-6)]GlcN(b)-O-TBDPS；(2S,3R,4R,5S,6R)-2-[tert-butyl(diphenyl)silyl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-amine
• 化学式: C₄₃H₄₉NO₅Si
• 分子量: 687.951
• InChiKey: DYTYLVRCCPZBRS-MHBOMZLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.0
• 重原子数：
  50
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyldiphenylsilyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranose 在 四丁基氟化铵 、 caesium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 24.5h， 生成 3,4,6-tri-O-benzyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-D-glucopyranosyl N-(phenyl)trifluoroacetimidate
  参考文献：
  名称：

  Synthesis of Differentially Protected Glucosamine Building Blocks and Their Evaluation as Glycosylating Agents

  摘要：

  The modular assembly of heparin oligosaccharides requires glucosamine building blocks with amine protecting groups for a-selective glycosylations that can be readily removed. The synthesis of N-4-nitrobenzensulphonamide (nosyl)- and N-2,4-dinitrophenyl (DNP)-protected glucosamine building blocks and their evaluation as glycosylating agents is described. The N-nosyl-protected glucosamine building blocks were challenging to prepare and their glycosylations resulted in inseparable mixtures of products. The N-DNP-protected glucosamines, however, were readily synthesized and resulted in a-selective couplings to protected L-iduronic acid derivatives.

  DOI：

  10.1080/07328300903105108
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-{[(4-methoxyphenyl)methylidene]amino}-D-glucopyranose 在 咪唑 、 甲醇 、 乙醇 、 氨 、 sodium 、 四丁基碘化铵 、 sodium hydride 、 溶剂黄146 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 mineral oil 为溶剂， 反应 10.0h， 生成 tert-butyldiphenylsilyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of Differentially Protected Glucosamine Building Blocks and Their Evaluation as Glycosylating Agents

  摘要：

  The modular assembly of heparin oligosaccharides requires glucosamine building blocks with amine protecting groups for a-selective glycosylations that can be readily removed. The synthesis of N-4-nitrobenzensulphonamide (nosyl)- and N-2,4-dinitrophenyl (DNP)-protected glucosamine building blocks and their evaluation as glycosylating agents is described. The N-nosyl-protected glucosamine building blocks were challenging to prepare and their glycosylations resulted in inseparable mixtures of products. The N-DNP-protected glucosamines, however, were readily synthesized and resulted in a-selective couplings to protected L-iduronic acid derivatives.

  DOI：

  10.1080/07328300903105108

文献信息

• Selective<i>N</i>-Sulfation of Glucosamine Derivatives using Phenyl Chlorosulfate in Non-Aqueous Solvent
  作者：Robert J. Kerns、Robert J. Linhardt

  DOI：10.1080/00397919608004583

  日期：1996.7

  Abstract The selective N-sulfation of 2-amino-2-deoxy-D-glucopyranose derivatives having unprotected hydroxyl groups with phenyl chlorosulfate and triethylamine in anhydrous organic solvent followed by addition of aqueous sodium bicarbonate affords high yields of the 2-deoxy-2-sulfoamino-D-glucopyranose products.

  摘要 在无水有机溶剂中用氯硫酸苯酯和三乙胺选择性 N-硫酸化具有未保护羟基的 2-氨基-2-脱氧-D-吡喃葡萄糖衍生物，然后加入碳酸氢钠水溶液，得到高产率的 2-脱氧-2-磺氨基-D-吡喃葡萄糖产品。
• Synthesis of Differentially Protected Glucosamine Building Blocks and Their Evaluation as Glycosylating Agents
  作者：Pascal Bindschadler、Lukas Dialer、Peter Seeberger

  DOI：10.1080/07328300903105108

  日期：2009.9

  The modular assembly of heparin oligosaccharides requires glucosamine building blocks with amine protecting groups for a-selective glycosylations that can be readily removed. The synthesis of N-4-nitrobenzensulphonamide (nosyl)- and N-2,4-dinitrophenyl (DNP)-protected glucosamine building blocks and their evaluation as glycosylating agents is described. The N-nosyl-protected glucosamine building blocks were challenging to prepare and their glycosylations resulted in inseparable mixtures of products. The N-DNP-protected glucosamines, however, were readily synthesized and resulted in a-selective couplings to protected L-iduronic acid derivatives.