allyl 2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside | 191925-41-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
• CAS: 191925-41-4
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: ZSSWHJUQNUJYIC-SJJUBHFPSA-N

物化性质

• 沸点：
  492.1±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.72
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.17
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  allyl 2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 在 sodium hydride 、 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 2.75h， 生成 allyl 2-amino-4,6-O-benzylidene-2,3-N,O-carbonyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Versatile and self-assembling urea-linked neosaccharides from sugar aminoalcohols

  摘要：

  The increasing interest in urea compounds as self-assembling molecules, ion transporters and organo-catalysts prompted several efforts towards synthetic urea-linked glycomimetics. In this frame we studied in details a novel two steps dimerization reaction of sugar vicinal aminoalcohol building blocks, opening a synthetic path to a series of urea-linked neosaccharides. Glucosamine neodisaccharide possessing an oxazolidinone-urea-oxazolidinone system could be transformed into both cyclic and higher linear neosaccharides. Furthermore, a series of six urea-linked glucosamine and galactosamine neodisaccharides was tested for self-assembling properties by measuring NMR spectra at different temperatures and concentrations as well as by gelation of several organic solvents. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.005
• 作为产物：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 L-camphorsulfonic acid 、 碳酸氢钠 、 溶剂黄146 、 乙酰氯 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.5h， 生成 allyl 2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  [EN] SILVER ASSISTED GOLD CATALYSIS FOR THE PREPARATION OF FONDAPARINUX PENTASACCHARIDE AND INTERMEDIATES
  [FR] CATALYSE À L'OR ASSISTÉE PAR L'ARGENT POUR LA PRÉPARATION DE PENTASACCHARIDE DE FONDAPARINUX ET D'INTERMÉDIAIRES

  摘要：

  本发明涉及一种合成Fondaparinux五糖及其中间体的过程。具体而言，本发明涉及一种新型催化合成Fondaparinux五糖及其中间体的过程。本发明还涉及在合成Fondaparinux五糖及其中间体的糖基化反应中使用银辅助金催化的方法。

  公开号：

  WO2022107013A1

文献信息

• A Urea-Linked Glucosamine Dimer as a Building Block for the Synthesis of Linear and Cyclic Neosaccharides
  作者：Luigi Cirillo、Alba Silipo、Emiliano Bedini、Michelangelo Parrilli

  DOI：10.1002/ejoc.201000292

  日期：2010.7

  A novel urea-linked glucosamine dimer was obtained through a modification of the standard oxazolidinone closure reaction on a 2,3-amino alcohol monomer and fully characterized by NMR spectroscopy and by molecular mechanics and dynamics techniques. A mechanism was proposed for the dimerization reaction that was based on the formation of a 2,3-bis[(p-nitrophenoxy)carbonyl] intermediate. Chemoselective

  通过对 2,3-氨基醇单体的标准恶唑烷酮闭合反应的修改，获得了一种新型的脲连接葡糖胺二聚体，并通过 NMR 光谱和分子力学和动力学技术进行了充分表征。提出了一种基于形成 2,3-双[(对硝基苯氧基)羰基] 中间体的二聚反应机制。对二聚体正交保护基团模式的化学选择性操作——尤其是在其前所未有的恶唑烷酮-脲-恶唑烷酮系统上——提供了一种醇结构单元，可用于获得更高的线性和环状新糖。新型氨基甲酸酯连接的新二糖大环的构象特征和 3D 表征是通过分子力学和动力学计算完成的。
• <i>O</i>- and <i>N</i>-Sulfations of Carbohydrates Using Sulfuryl Imidazolium Salts
  作者：Laura J. Ingram、Ahmed Desoky、Ahmed M. Ali、Scott D. Taylor

  DOI：10.1021/jo9014112

  日期：2009.9.4

  A series of sulfuryl imidazolium salts (SISs) were prepared and examined as reagents for incorporating trichloroethyl-protected sulfate esters into carbohydrates. The SIS that contained a 1,2-dimethylimidazolium moiety (SIS 9) proved to be a superior sulfating compared to SISs bearing no alkyl groups or bulkier alkyl groups on the imidazolium ring. Difficult O-sulfations that required prolonged reaction times and a large excess of the SIS bearing a 1-methylimidazolium group (SIS 5) were achieved in high yield using less than half the amount of SIS 9 in less time. Certain N-sulfated compounds that were practically inaccessible using SIS 5 were obtained in excellent yield using SIS 9.
• Potential HIV protease inhibitors: Preparation of di-N-alkylated 2-, 6-, and 2,6-aminodeoxy-derivatives of d-glucose by direct displacement and by a novel reductive-alkylation procedure
  作者：Jiaqiang Cai、Bruce E. Davison、C.Robin Ganellin、Suvit Thaisrivongs、Keith S. Wibley

  DOI：10.1016/s0008-6215(97)00039-6

  日期：1997.5

  Glucose derivatives carrying branched lipophilic groups at the 2-, 6-, and 2,6-positions were required for biological testing as inhibitors of the protease produced by the human immunodeficiency virus. The synthesis of (N-benzyl-N-ethyl)-2-, 6- and 2,6-diaminodeoxy-D-glucose derivatives is described. The 2-tert-amino group was introduced by a two-step reductive alkylation procedure. The novel tertiary aminosugar, 2,6-di-(N-benzyl-N-ethyl)amino-2,6-dideoxy-D-glucose, was made via direct substitution of the sulphonate group in allyl 2-acetamido-2-deoxy-6-O-tosyl-D-glucopyranoside with N-benzylethylamine. (C) 1997 Elsevier Science Ltd.
• Synthesis of a β-GlcN-(1→4)-MurNAc building block en route to N-deacetylated peptidoglycan fragments
  作者：Luigi Cirillo、Emiliano Bedini、Antonio Molinaro、Michelangelo Parrilli

  DOI：10.1016/j.tetlet.2009.12.124

  日期：2010.2

  Some bacteria present a variation in their peptidoglycan structure that is the absence of the N-acetyl substituent in the glucosamine residue. Very recently, this structural modification was demonstrated to be critical for host innate immune evasion in Listeria monocytogenes. To shed light on the molecular details of the evasion mechanism, the synthesis of some N-deacetylated peptidoglycan fragments is needed. En route to this goal a high-yielding synthesis of a GlcN-MurNAc disaccharide building block has been accomplished. A careful study of the optimal protecting groups and reaction conditions was done to have a complete beta-stereoselectivity in glycosylation as well as to ensure a high versatility to the disaccharide building block. (C) 2009 Elsevier Ltd. All rights reserved.