2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl amine | 33639-91-7

• 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: 2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl amine
• 英文别名: Bn4-β-D-Man-NH2；[(2R,3R,4S,5S,6R)-6-amino-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 33639-91-7；108967-44-8；115969-98-7；41093-31-6
• 化学式: C₃₄H₂₉NO₉
• 分子量: 595.606
• InChiKey: YYMRIRHNWASDCW-IXYVTWBDSA-N

物化性质

• 沸点：
  731.8±60.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl amine 在 N-乙基吗啉 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 tert-butyl N-{(2S)-2-hydroxy-1-oxo-3-[3-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)ureido]propyl}phenylalaninate
  参考文献：
  名称：

  Hexafluoroacetone as a Protecting and Activating Reagent. N- and O-Glycosylation of Isoserine and Isocysteine

  摘要：

  Starting from HFA-protected malic and thiomalic acid a series of O- and N-glycoconjugates suitable for peptide and depsipeptide modification has been synthesized.

  DOI：

  10.1007/s00706-004-0248-9
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl azide 在 platinum(IV) oxide 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 以100%的产率得到2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl amine
  参考文献：
  名称：

  Synthesis of β-Glycosyl Amides from N-Glycosyl Dinitrobenzenesulfonamides

  摘要：

  The N-glycosyl-2,4-dinitrobenzenesulfonamides were accessed via benzoyl-protected beta-glycosyl azides. The azides were reduced with Adams' catalyst to the corresponding amines. The glycosylamines were sulfonated with 2,4-dinitrobenzenesulfonyl chloride to form N-glycosyl-2,4-dinitrobenzenesulfonamides in moderate yields. beta-Glycosyl amides were then prepared in 67% to 81% yields by treatment of the sulfonamides with thioacetic acid and cesium carbonate. The conversion of the glycosylsulfonamide to the glycosyl amide proceeded with high stereoselectivity.

  DOI：

  10.1080/07328303.2012.663431

文献信息

• Synthesis and characterization of mannosyl mimetic derivatives based on a β-cyclodextrin core
  作者：Duplex Yockot、Vincent Moreau、Gilles Demailly、Florence Djedaïni-Pilard

  DOI：10.1039/b301670f

  日期：——

  The synthesis of branched β-cyclodextrins substituted with mannosyl mimetic derivatives at one primary hydroxy group is described. It was shown that the self-inclusion phenomenon observed for the target compounds in water did not preclude the inclusion properties of the cyclodextrin moiety.

  本研究介绍了在一个伯羟基上被甘露糖基拟态衍生物取代的支链δ-环糊精的合成。研究表明，目标化合物在水中的自包容现象并不排除环糊精分子的包容特性。
• A convenient microwave-assisted synthesis of N-glycosyl amino acids
  作者：Ilaria Paolini、Francesca Nuti、Maria de la Cruz Pozo-Carrero、Francesca Barbetti、Beata Kolesinska、Zbigniew J. Kaminski、Mario Chelli、Anna M. Papini

  DOI：10.1016/j.tetlet.2007.02.087

  日期：2007.4

  Optimization of coupling reactions of glycosylamines with Fmoc-protected aspartic acid, by microwave approach, is described. Different reaction conditions, quantities of substrates and solvents were tested to develop simple and reproducible methodologies. The best results were obtained using new triazine-based coupling reagents with a monomode microwave Discover (R) BenchMate (TM) instrument (CEM). The N-glycosyl amino acids were then deprotected to achieve final products for SPPS. (c) 2007 Elsevier Ltd. All rights reserved.