2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl azide | 41093-30-5

• 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 azide
• 英文别名: [(2R,3R,4S,5S,6R)-6-azido-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 41093-30-5
• 化学式: C₃₄H₂₇N₃O₉
• 分子量: 621.603
• InChiKey: SHZKMJFYJDZFHE-IXYVTWBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl azide 在 甲醇 、 sodium methylate 作用下， 生成 β-D-Mannopyranosyl azide
  参考文献：
  名称：

  6-氨基-1,6-脱水-6-脱氧糖衍生物的合成

  摘要：

  摘要三苯基膦与2,3,4-三-O-乙酰基-6-O-对甲苯磺酰基-β-d-糖基叠氮基叠氮化物的斯托丁格反应导致了端基异亚氨基正膦，该异位亚氨基正膦通过消除C-6处的磺酸盐而原位重排。将如此获得的1，6-脱水-6-脱氧-6-三苯基膦酰氨基-β-d-甘露糖盐转化为相应的2,3,4-三-O-乙酰基-6-氨基-1,6-脱水-盐。进一步被N-酰化或N-烷氧基羰基化的6-脱氧-β-d-甘露聚糖。这些产物的1 H和13 C NMR表明，由于酰胺键周围的旋转受限，在溶液中存在两个旋转异构体。

  DOI：

  10.1016/s0008-6215(98)00089-5
• 作为产物：
  描述：

  2-(乙酰氧基甲基)-6-叠氮基四氢-2H-吡喃-3,4,5-三基三乙酸酯 在 吡啶 、 甲醇 、 sodium 作用下， 反应 16.0h， 生成 2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl azide
  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

• 'Click' Preparation of Carbohydrate 1-Benzotriazoles, 1,4-Disubstituted, and 1,4,5-Trisubstituted Triazoles and their Utility as Glycosyl Donors
  作者：Jacinta A. Watt、Carlie T. Gannon、Karen J. Loft、Zoran Dinev、Spencer J. Williams

  DOI：10.1071/ch08364

  日期：——

  azides using benzynes derived from substituted anthranilic acids. The reactivity of the resulting anomeric 1-benzotriazoles as glycosyl donors was investigated and compared with 1,4-disubstituted glycosyl triazoles (from the CuAAC reaction) and 1,4,5-trisubstituted glycosyl triazoles (prepared by Huisgen cycloaddition of glycosyl azides and dimethyl acetylene dicarboxylate). The 1,4,5-trisubstituted

  糖基三唑可以通过各种“点击”方法从现成的异头叠氮化物制备：与炔烃的热Huisgen 环加成、苯炔的应变促进Huisgen 环加成和CuI 催化的末端炔烃的叠氮化物-炔烃环加成（CuAAC 反应）。在这里，我们研究了使用衍生自取代邻氨基苯甲酸的苯炔从异头和非异头碳水化合物叠氮化物形成糖基 1-苯并三唑。研究了生成的异头 1-苯并三唑作为糖基供体的反应性，并与 1,4-二取代的糖基三唑（来自 CuAAC 反应）和 1,4,5-三取代的糖基三唑（通过糖基叠氮化物和二甲基的 Huisgen 环加成制备）进行了比较乙炔二羧酸盐）。1,4, 5-三取代的糖基三唑被路易斯酸活化，可以转化为 O-糖苷、S-糖苷、糖基氯化物和糖基叠氮化物。相比之下，在所研究的所有条件下，1,4-二取代的糖基三唑类作为糖基供体都没有反应性。糖基 1-苯并三唑作为糖基供体通常是惰性的；然而，在苯并三唑基团上带有吸电子取代基的四
• Glycoprotein Mimics with Tunable Functionalization through Global Amino Acid Substitution and Copper Click Chemistry
  作者：Brian M. Seifried、Wenjing Qi、Yun Jung Yang、Danielle J. Mai、Wendy B. Puryear、Jonathan A. Runstadler、Guosong Chen、Bradley D. Olsen

  DOI：10.1021/acs.bioconjchem.9b00601

  日期：2020.3.18

  that form a densely grafted protein-polysaccharide brush architecture. Herein a new approach to protein bioconjugate synthesis is demonstrated that can approach the functionalization densities of natural glycoproteins through oligosaccharide grafting. Global amino acid substitution is used to replace the methionine residues in a methionine-enriched elastin-like polypeptide with homopropargylglycine (HPG);

  糖蛋白及其模拟物的生产具有挑战性，因为它们的大量多糖侧链形成了密集嫁接的蛋白-多糖刷结构。本文证明了一种新的蛋白质生物共轭物合成方法，该方法可以通过寡糖接枝接近天然糖蛋白的功能化密度。全局氨基酸取代用于用高炔丙基甘氨酸（HPG）代替富含蛋氨酸的弹性蛋白样多肽中的蛋氨酸残基；发现该取代取代了蛋白质序列中41个蛋氨酸中的93％，并加宽并增加了热响应转变。通过铜（I）催化的炔-叠氮化物环加成反应将一系列糖与重组蛋白主链偶联，以确定反应性趋势，HPG的糖基化率为83-100％。仅乙酰基保护的唾液乳糖部分显示出较低水平的42％HPG糖基化，这归因于位阻。重组糖蛋白复制了其天然对应物的关键生物功能特性，例如病毒抑制和凝集素结合。
• A novel synthesis of β-d-mannopyranosyl azide by phase transfer catalysis
  作者：Polina I. Abronina、Vadim V. Kachala、Leonid O. Kononov

  DOI：10.1016/j.carres.2008.10.027

  日期：2009.1

  simple stereoselective synthesis of per-O-benzoyl-beta-d-mannopyranosyl azide from per-O-benzoyl-alpha-d-mannopyranosyl bromide using phase transfer catalysis was developed. The stereochemistry at C-1 of the anomeric O-benzoylated alpha- and beta-d-mannopyranosyl azides was unambiguously established using 2D NOESY NMR spectroscopy. Pure deprotected beta-d-mannopyranosyl azide was prepared by debenzoylation

  建立了一种简单的立体选择性合成方法，采用相转移催化从全邻苯甲酰基-α-d-甘露聚糖基溴化物合成全邻苯甲酰基-β-d-甘露聚糖基叠氮化物。使用2D NOESY NMR光谱学可以明确地确定异头O-苯甲酰化的α-和β-d-甘露吡喃糖基叠氮化物在C-1处的立体化学。通过在甲醇中用甲醇钠进行脱苯甲酰化反应，可以制得纯的脱保护的β-d-甘露聚糖基叠氮化物。
• Synthesis of β-Glycosyl Amides from <i>N</i>-Glycosyl Dinitrobenzenesulfonamides
  作者：Vishwanath Gaitonde、Steven J. Sucheck

  DOI：10.1080/07328303.2012.663431

  日期：2012.5.1

  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.
• Synthesis of 6-amino-1,6-anhydro-6-deoxysugar derivatives
  作者：Dominique Lafont、Andreas Wollny、Paul Boullanger

  DOI：10.1016/s0008-6215(98)00089-5

  日期：1998.8

  lphosphonioamino- β - d -glycopyranose salts thus obtained were transformed into the corresponding 2,3,4-tri- O -acetyl-6-amino-1,6-anhydro-6-deoxy- β - d -glycopyranoses which were further N -acylated or N -alkoxycarbonylated. 1 H and 13 C NMR of these products show the occurrence of two rotamers in solution, due to restricted rotations around the amide bond.

  摘要三苯基膦与2,3,4-三-O-乙酰基-6-O-对甲苯磺酰基-β-d-糖基叠氮基叠氮化物的斯托丁格反应导致了端基异亚氨基正膦，该异位亚氨基正膦通过消除C-6处的磺酸盐而原位重排。将如此获得的1，6-脱水-6-脱氧-6-三苯基膦酰氨基-β-d-甘露糖盐转化为相应的2,3,4-三-O-乙酰基-6-氨基-1,6-脱水-盐。进一步被N-酰化或N-烷氧基羰基化的6-脱氧-β-d-甘露聚糖。这些产物的1 H和13 C NMR表明，由于酰胺键周围的旋转受限，在溶液中存在两个旋转异构体。