1,5-anhydro-2,3,4,6-tetra-O-benzyl-D-glucitol | 78890-68-3

• 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: 1,5-anhydro-2,3,4,6-tetra-O-benzyl-D-glucitol
• 英文别名: (2R,3R,4R,5S)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)oxane
• CAS: 78890-68-3
• 化学式: C₃₄H₃₆O₅
• 分子量: 524.657
• InChiKey: QKZMWYJFJHCINI-KMKAFXEASA-N

物化性质

• 沸点：
  640.3±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-2,3,4,6-tetra-O-benzyl-D-glucitol 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙醇 为溶剂， 反应 29.0h， 生成 1,5-anhydro-6-O-trityl-D-glucitol
  参考文献：
  名称：

  A New Strategy for the Stereoselecitve Syntheses of C-Glycosyl Compounds of β-Pentapyranoses

  摘要：

  The C-glycosyl compounds of beta-L-xylopyranose and beta-D-arabinopyranose were conveniently prepared by reduction of methyl alpha-D-glucopyranoside and methyl alpha-D-mannopyranoside with triethylsilane in the presence of trimethylsilyl trifluoromethanesulfonate, respectively.

  DOI：

  10.1080/00397919608003565
• 作为产物：
  描述：

  p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside 在 二氢吡啶 作用下， 以 1,4-二氧六环 为溶剂， 以72%的产率得到1,5-anhydro-2,3,4,6-tetra-O-benzyl-D-glucitol
  参考文献：
  名称：

  Additive-controlled synthesis of 1- and 2-deoxysugars from thioglycosides

  摘要：

  DOI：

  10.1080/07328303.2021.2015366

文献信息

• C-nucleoside studies. Part 13. A new synthesis of 2,3,5-tri-O-benzyl-α(and β)-<scp>D</scp>-ribofuranosylethyne involving benzyloxy participation, and a synthesis of α-showdomycin
  作者：Gaffar Aslani-Shotorbani、J. Grant Buchanan、Alan R. Edgar、Colin T. Shanks、Gavin C. Williams

  DOI：10.1039/p19810002267

  日期：——

  when the intermediate 2,3,4,6-tetra-O-toluene-p-sulphonyl-D-glucitol (6) is converted into its 0–5 oxyanion. Benzyloxy participation has been exploited in a new synthesis of 2,3,5-tri-O-benzyl-α(and β)-D-ribofuranosylethyne, (20) and (4), from 2,3,4,5-tetra-O-benzyl-aldehydo-D-ribose. A synthesis of 2-α-D-ribofuranosylmaleimide, the α-isomer of showdomycin, from (20) is described.

  2,3,4,6-四- ö苄基d -glucitol（5）反应以甲苯p -磺酰基氯在吡啶中于60℃，以形成主要是呋喃产物2,3,6-三ö -苄基-1,4-脱水-D-葡萄糖醇（10）及其5-甲苯-对磺酸酯（11），但失去4- O-苄基。该吡喃产物四ö苄基1,5-脱水- d -glucitol preponderates当中间2,3,4,6-四ö -toluene- p -sulphonyl- d -glucitol（6）转化成其0–5氧阴离子。在新合成的2,3,5-tri- O中已经利用了苄氧基的参与苄基α（及β） - d -ribofuranosylethyne，（20）和（4），从2,3,4,5-四ö苄基醛基- d -核糖。描述了由（20）合成2-α- D-呋喃呋喃糖基马来酰亚胺（Showdomycin的α-异构体）。
• [EN] REAGENTS AND METHODS FOR GLYCOSYLATION<br/>[FR] RÉACTIFS ET MÉTHODES DE GLYCOSYLATION
  申请人：UNIV FLORIDA

  公开号：WO2018035416A1

  公开（公告）日：2018-02-22

  The invention provides methods and regents for the glycosylation of organic molecules. In one aspect, the invention provides a method for glycosylating a hydroxyl-containing organic compound (i.e., a glycosyl acceptor) comprising contacting a glycosyl donor with the hydroxyl-containing organic compound, in the presence of an oxidant, to yield a glycosylated organic compound. In certain embodiments, the methods provided herein provide glycosylation products with high anomeric selectivity. The methods can be applied to the synthesis of disaccharides, trisaccharides, polysaccharides, glycans, etc. Also provided herein are compounds (e.g., glycosyl donors and acceptors) which are useful building blocks in the provided reactions.

  这项发明提供了一种用于有机分子的糖基化的方法和试剂。在一个方面，该发明提供了一种用于糖基化含有羟基的有机化合物（即糖基受体）的方法，包括将糖基供体与含有羟基的有机化合物在氧化剂存在下接触，以产生糖基化的有机化合物。在某些实施例中，本文提供的方法提供了高各向异性选择性的糖基化产物。这些方法可以应用于二糖、三糖、多糖、糖类等的合成。本文还提供了在所述反应中有用的化合物（例如，糖基供体和受体），这些化合物是提供的反应中的构建模块。
• Synthesis of α-C-Glycosides by Samarium Diiodide Mediated Coupling of Glycosyl Pyridyl Sulfones with Alkenes
  作者：Xin-Shan Ye、Gen Li、De-Cai Xiong

  DOI：10.1055/s-0030-1261230

  日期：2011.10

  A mild method for the synthesis of α-C-glycosides by the samarium diiodide mediated coupling reactions of glycosyl 2-pyridyl sulfones with different α,β-unsaturated carbonyl compounds has been developed. This method allows the use of less amount of substrates. C-glycosides - samarium diiodide - glycosyl 2-pyridyl sulfones - coupling reaction

  已经开发了一种温和的方法，该方法通过二碘化sa介导的糖基2-吡啶基砜与不同的α，β-不饱和羰基化合物的偶联反应合成α- C-糖苷。该方法允许使用较少量的基板。 C-糖苷-二碘化mar-糖基2-吡啶基砜-偶联反应
• CuBr₂-catalyzed diastereoselective allylation: total synthesis of decytospolides A and B and their C6-epimers
  作者：Birakishore Padhi、G. Sudhakar Reddy、N. Arjunreddy Mallampudi、Utkal Mani Choudhury、Debendra K. Mohapatra

  DOI：10.1039/c9ob02689d

  日期：——

  CuBr2-catalyzed diastereoselective allylation of a cyclic hemiacetal with allyltrimethylsilane as a nucleophile has been developed. The protocol offers a cost effective, protecting group tolerant, and operationally simple approach to 2,6-trans-disubstituted tetrahydropyran with excellent diastereoselectivity. Furthermore, the application of this methodology has been demonstrated in the total synthesis of decytospolides

  已经开发了有效的CuBr 2催化的半缩醛与烯丙基三甲基硅烷作为亲核试剂的非对映选择性烯丙基化。该协议为2,6-反式-双取代的四氢吡喃提供了具有成本效益的，具有保护基团耐受性的且操作简便的方法，具有出色的非对映选择性。此外，这种方法的应用已在脱细胞肽A和B及其C6-表位分子的全合成中得到证明。
• Reactions of glycosyl fluorides. Synthesis of C-glycosides
  作者：K. C. Nicolaou、Roland E. Dolle、Alexander Chucholowski、Jared L. Randall

  DOI：10.1039/c39840001153

  日期：——

  Glycosyl fluorides were found to react with a number of nucleophilic reagents with or without catalysis leading to a variety of C-glycosides and related compounds.

  发现糖基氟化物在催化作用或不催化作用下与许多亲核试剂反应，从而导致多种C-糖苷和相关化合物。