2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosylamine

• 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-galactopyranosylamine
• 英文别名: (2R,3R,4S,5S,6R)-2-amino-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate；[(2R,3S,4S,5R,6R)-6-amino-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• 化学式: C₃₄H₂₉NO₉
• 分子量: 595.606
• InChiKey: YYMRIRHNWASDCW-HBMYTODVSA-N

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-galactopyranosylamine 在 吡啶 、 4-二甲氨基吡啶 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 (2R,3R,4S,5S,6R)-2-acetamido-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
  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
• 作为产物：
  描述：

  1-叠氮-1-脱氧-β-D-吡喃半乳糖苷 在 吡啶 、 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 15.5h， 生成 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosylamine
  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

• Facile and efficient access to C1-aminosugar derivatives under mild conditions
  作者：Mengbi Guo、Xin Wang、Yitong Wang、Zhuang Hou、Chun Guo、Ping Gong

  DOI：10.1016/j.tetlet.2022.153644

  日期：2022.2

  A facile and efficient synthesis of C1-aminosugar derivatives under catalyst-free conditions is described here. In particular, readily available benzoyl glycosyl bromides react smoothly to give a broad scope of C1-aminosugar derivatives in good yields. The present method proves to be efficient and facile in terms of short reaction time, high yield and the broad substrate scope.

  本文描述了在无催化剂条件下简便有效地合成 C1-氨基糖衍生物。特别是，容易获得的苯甲酰溴化糖可以平稳地反应，以良好的收率产生范围广泛的 C1-氨基糖衍生物。本方法在反应时间短、产率高和底物范围广等方面证明是有效和简便的。
• Synthesis of Thioureido-Linked Peptidomimetics, Glycosylated Amino Acids, and Neoglycoconjugates Using Bis(benzotriazolyl)methanethione as Thioacylating Agent
  作者：Vommina Sureshbabu、Gundala Chennakrishnareddy、Hosahalli Hemantha

  DOI：10.1055/s-0029-1219393

  日期：2010.3

  A practical synthesis of thiourea-linked peptidomimetics, glycosylated amino acids, and neoglycoconjugates is described employing bis(benzotriazolyl)methanethione as thiocarbonylating reagent. The entire protocol is mild, efficient, high-yielding, and free from hazardous reagents. All the intermediates and products have been isolated and fully characterized by ¹H NMR, ¹³C NMR, and mass spectrometry.

  本文描述了一种实用的硫脲连接肽模拟物、糖基化氨基酸和新生糖缀合物的综合合成方法，采用双（苯并三唑基）甲烷硫酮作为硫羰基化试剂。整个方案温和、高效、产率高，并且不含危险试剂。所有中间体和产物均已分离并通过¹H NMR、¹³C NMR 和质谱完全表征。
• One-Pot Synthesis of Ureido Peptides and Urea-Tethered Glycosylated Amino Acids Employing Deoxo-Fluor and TMSN3
  作者：V. Sureshbabu、H. Hemantha、G. Chennakrishnareddy、T. Vishwanatha

  DOI：10.1055/s-0028-1087538

  日期：2009.2

  urea-linked peptidomimetics and neoglycopeptides under Curtius rearrangement conditions employing Deoxo-Fluor and TMSN3 is described. The method is efficient and circumvents the isolation of acyl azide and isocyanate intermediates. The rearrangement of the in situ generated acyl azide via the acyl fluoride was carried out under ultrasonication followed by amine capture to insert a urea bond. The protocol

  描述了一种简便的一锅法，用于在使用 Deoxo-Fluor 和 TMSN3 的 Curtius 重排条件下合成尿素连接的肽模拟物和新糖肽。该方法有效并且避免了酰基叠氮化物和异氰酸酯中间体的分离。在超声处理下通过酰氟对原位生成的酰基叠氮化物进行重排，然后进行胺捕获以插入脲键。该方案适用于所有常见的 N-氨基甲酸乙酯保护的氨基酸以及糖 6-酸。© Georg Thieme Verlag 斯图加特。
• Synthesis of Hybrid Peptidomimetics and Neoglycoconjugates Employing Click Protocol: Dual Utility of Poc-Group for Inserting Carbamate-Triazole Units into Peptide Backbone
  作者：Hosahalli P. Hemantha、Ravi S. Lamani、Vommina V. Sureshbabu

  DOI：10.1007/s10989-010-9228-6

  日期：2010.12

  Synthesis of new types of peptidomimetics and glycosylated amino acids possessing 1,2,3-triazole and carbamate moieties is described. Poc-protected amino acid esters/1-amino sugars were subjected to Cu(I) catalyzed [2+3]cycloaddition with desired azides under click protocol to obtain novel peptide and carbohydrate mimetics. The reaction is rapid, efficient and all the products are isolated in good yield and excellent purity.

  描述了新型肽类似物和具有1,2,3-三唑和氨基甲酸酯基团的糖基氨基酸的合成。经Poc保护的氨基酸酯/1-氨基糖在点击反应条件下与所需的叠氮化合物进行Cu(I)催化的[2+3]环加成反应，以获得新型的肽和碳水化合物类似物。该反应快速、高效，所有产物均以良好的产率和优异的纯度分离得到。
• Nagendra; Hemantha; Sureshbabu, Vommina V., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 3, p. 397 - 407
  作者：Nagendra、Hemantha、Sureshbabu, Vommina V.

  DOI：——

  日期：——