methyl (phenyl 2,3-di-O-benzoyl-1-thio-β-D-glucopyranosid)uronate | 725228-76-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (phenyl 2,3-di-O-benzoyl-1-thio-β-D-glucopyranosid)uronate
• 英文别名: methyl (2S,3S,4S,5R,6S)-4,5-dibenzoyloxy-3-hydroxy-6-phenylsulfanyloxane-2-carboxylate
• CAS: 725228-76-2
• 化学式: C₂₇H₂₄O₈S
• 分子量: 508.549
• InChiKey: OSRDPWAHVFTVEA-NHEZYTHKSA-N

物化性质

• 沸点：
  675.6±55.0 °C(predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (phenyl 2,3-di-O-benzoyl-1-thio-β-D-glucopyranosid)uronate 在 4-二甲氨基吡啶 、 间氯过氧苯甲酸 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 methyl 2,3-di-O-benzoyl-1-deoxy-4-O-levulinoyl-1-(phenylsulfinyl)-β-D-glucopyranosyluronate
  参考文献：
  名称：

  潜在的10E4四糖抗原涉及Scrapie发病机理的合成。

  摘要：

  为了检验四糖3参与瘙痒病发病机理的假说，合成了在还原端用胺连接基官能化的四糖衍生物32。选择（2 + 2）糖基化方法以完全保护的形式提供目标化合物。为了研究其生物学作用，使用Traut试剂将四糖32进一步官能化为相应的硫醇33。在合成过程中，N，N-二乙酰基保护基被证明对自由基和酸性条件不稳定。

  DOI：

  10.1002/hlca.200690234
• 作为产物：
  描述：

  phenyl 2,3-di-O-benzoyl-1-thio-β-D-glucopyranoside 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 作用下， 以 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 methyl (phenyl 2,3-di-O-benzoyl-1-thio-β-D-glucopyranosid)uronate
  参考文献：
  名称：

  Thioglycuronides:  Synthesis and Application in the Assembly of Acidic Oligosaccharides

  摘要：

  Partially protected thioglycuronic acids are prepared efficiently by chemo- and regioselective oxidation of the corresponding thioglycosides using the TEMPO/BAIB reagent combination. After esterification, the thioglycuronic acids proved to be useful as both donor and acceptor in sulfonium-mediated condensations toward acidic di- and trisaccharides.

  DOI：

  10.1021/ol049380+

文献信息

• Automated Solid-Phase Synthesis of Hyaluronan Oligosaccharides
  作者：Marthe T. C. Walvoort、Anne Geert Volbeda、Niels R. M. Reintjens、Hans van den Elst、Obadiah J. Plante、Herman S. Overkleeft、Gijsbert A. van der Marel、Jeroen D. C. Codée

  DOI：10.1021/ol301666n

  日期：2012.7.20

  Well-defined fragments of hyaluronic acid (HA) have been obtained through a fully automated solid-phase oligosaccharide synthesis. Disaccharide building blocks, featuring a disarmed glucuronic acid donor moiety and a di-tert-butylsilylidene-protected glucosamine part, were used in the rapid and efficient assembly of HA fragments up to the pentadecamer level, equipped with a conjugation-ready anomeric

  透明质酸（HA）的明确片段已通过全自动固相寡糖合成获得。具有糖基葡萄糖醛酸供体部分和二叔丁基亚甲叉基保护的葡糖胺部分的二糖结构单元可用于快速有效地组装HA片段，使其达到十五烷水平，并具有可结合的异头烯丙基功能。
• A practical synthesis of capped 4-methylumbelliferyl hyaluronan disaccharides and tetrasaccharides as potential hyaluronidase substrates
  作者：Henrik Gold、Stefan Munneke、Jasper Dinkelaar、Herman S. Overkleeft、Johannes M.F.G. Aerts、Jeroen D.C. Codée、Gijs A. van der Marel

  DOI：10.1016/j.carres.2011.03.042

  日期：2011.9

  The synthesis of hyaluronan dimers and tetramers equipped with a 4-methylumbelliferyl group at the reducing end to potentially allow monitoring of hyaluronidase activities is described. The 4-OH at the non-reducing glucuronate in the presented series is either removed or methylated to prohibit transglycosylase reactions, leading to a total of four probes. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of Hyaluronic Acid Oligomers using Chemoselective and One-Pot Strategies
  作者：Jasper Dinkelaar、Henrik Gold、Herman S. Overkleeft、Jeroen D. C. Codée、Gijsbert A. van der Marel

  DOI：10.1021/jo9003713

  日期：2009.6.5

  An efficient synthetic strategy toward a hyaluronic acid (HA) tri-, penta-, and heptamer having a glucosamine-reducing end is reported. The synthesis is based on a glucuronate ester thioglycoside and a trifluoro-N-phenylimidate glucosamine building block. The HA-fragments are synthesized using an S-phenyl GlcN-GluA building block through a combination of chemoselective and one-pot condensation strategies.
• Synthesis of Hyaluronic Acid Oligomers Using Ph₂SO/Tf₂O-Mediated Glycosylations
  作者：Jasper Dinkelaar、Jeroen D. C. Codée、Leendert J. van den Bos、Herman S. Overkleeft、Gijsbert A. van der Marel

  DOI：10.1021/jo070704s

  日期：2007.7.1

  The synthesis of hyaluronic acid (HA) oligomers using a stepwise glycosylation strategy is described. This method employs protected 1-hydroxyuronic acid and 1-phenylthio glucosamine donors, both of which are activated with the Ph2SO/Tf2O activator system.
• Synthesis of a Potential 10E4 Tetrasaccharide Antigen Involved in Scrapie Pathogenesis
  作者：Pascal Bindschädler、Christian Noti、Eva Castagnetti、Peter H. Seeberger

  DOI：10.1002/hlca.200690234

  日期：2006.11

  To test the hypothesis that tetrasaccharide 3 is involved in scrapie pathogenesis, tetrasaccharide derivative 32 functionalized with an amine linker at the reducing end was synthesized. A (2 + 2) glycosylation approach was chosen to furnish the target compound in fully protected form. To investigate its biological role, tetrasaccharide 32 was further functionalized to the corresponding thiol 33 using

  为了检验四糖3参与瘙痒病发病机理的假说，合成了在还原端用胺连接基官能化的四糖衍生物32。选择（2 + 2）糖基化方法以完全保护的形式提供目标化合物。为了研究其生物学作用，使用Traut试剂将四糖32进一步官能化为相应的硫醇33。在合成过程中，N，N-二乙酰基保护基被证明对自由基和酸性条件不稳定。