4,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl bromide | 67857-23-2

• 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: 4,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl bromide
• CAS: 67857-23-2
• 化学式: C₁₇H₂₀BrN₃O₆
• 分子量: 442.266
• InChiKey: PJSKKCOACFBAID-HHARLNAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  119.82
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl bromide 在 sodium methylate 、 silver perchlorate 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 Acetic acid (2R,3S,4R,5R,6R)-6-((1S,2R,3S,4S,5R,6S)-2-allyloxy-3,4,5,6-tetrakis-benzyloxy-cyclohexyloxy)-5-azido-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  A ready, convergent synthesis of the heptasaccharide GPI membrane anchor of rat brain Thy-1 glycoprotein

  摘要：

  DOI：

  10.1021/ja00070a048
• 作为产物：
  描述：

  1,4,6-tri-O-acetyl-2-azido-2-deoxy-3-O-benzyl-D-glucopyranose 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 3.5h， 以100%的产率得到4,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl bromide
  参考文献：
  名称：

  α:β Selectivity in the synthesis of 3-substituted, 4-methyl umbelliferone glycosides of N-acetyl glucosamine and chitobiose

  摘要：

  The influence of phenolic acceptor nucleophilicity; for example, 3-substituted, 4-methylumbelliferones, and glycosyl donor electrophilicity; for example, 3- and 4-substituted N-acetylglucosamines, on glycosylation stereochemistry has been evaluated. In a systematic comparison, the stereochemical outcome as well as the reaction yield appeared to be influenced by the 3- and 4-substituents of the donor as well as the 3-substituent of the aryl acceptor. In the context of synthesizing a fluorogenic substrate for oligosaccharyltransferase, an alpha-glycoside was desired. Although most acceptor-donor pairs led to predominantly or exclusively the beta-glycoside, reaction of the most activated (3,4-di-O-benzyl) donor and the least nucleophilic acceptor (3-Br), resulted in a 1:1 ratio of alpha,beta arylglycosides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.053

文献信息

• Studies Related to Synthesis of Glycophosphatidylinositol Membrane-Bound Protein Anchors. 6. Convergent Assembly of Subunits
  作者：Robert Madsen、Uko E. Udodong、Carmichael Roberts、David R. Mootoo、Peter Konradsson、Bert Fraser-Reid

  DOI：10.1021/ja00110a011

  日期：1995.2

  Glycophosphatidylinositol anchors of membrane-bound proteins are thought to comprise a common pentasaccharide core containing mannan, glucosamine, and inositol residues. A synthetic route to this core is described. In addition, the complete heptasaccharide moiety of the rat brain Thy-1 membrane anchor, the first mammalian membrane anchor to be characterized, has been synthesized. In the case of the Thy-1 anchor, the synthetic plan is based on three building blocks comprising glucosamine-inositol, galactosamine-mannose, and trimannan residues. Although glycosyl donors other than n-pentenyl glycosides (NPGs) have been used in preparing each of these building blocks, the final assembly of the heptasaccharide utilizes NPGs as the only glycosyl donors. The mildness of the conditions for these coupling reactions has allowed us to make provisions for subsequent installation of the three phosphodiester units.
• Paulsen, Hans; Huffziger, Axel; Boeckel, Constant A. A. van, Liebigs Annalen der Chemie, 1988, p. 419 - 426
  作者：Paulsen, Hans、Huffziger, Axel、Boeckel, Constant A. A. van

  DOI：——

  日期：——
• Boeckel, C. A. A. van; Beetz, T., Recueil des Travaux Chimiques des Pays-Bas, 1985, vol. 104, # 6, p. 174 - 176
  作者：Boeckel, C. A. A. van、Beetz, T.

  DOI：——

  日期：——