1,4,6-tri-O-acetyl-2-azido-2-deoxy-3-O-benzyl-D-glucopyranose | 163251-64-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,4,6-tri-O-acetyl-2-azido-2-deoxy-3-O-benzyl-D-glucopyranose
• 英文别名: 1,5,6-Tri-O-acetyl-2-azido-3-O-benzyl-2-deoxy-glucopyranose；1,4,6-tri-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose；1,4,6-tri-O-acetyl-3-O-benzyl-2-azido-2-deoxy-D-glucopyranose；[(2R,3S,4R,5R)-3,6-diacetyloxy-5-azido-4-phenylmethoxyoxan-2-yl]methyl acetate
• CAS: 163251-64-7
• 化学式: C₁₉H₂₃N₃O₈
• 分子量: 421.407
• InChiKey: CMWKJWYZWCPYKD-XTHKVDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  乙酸酐 、 4-O-acetyl-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 在 三氟乙酸 作用下， 反应 96.0h， 生成 1,4,6-tri-O-acetyl-2-azido-2-deoxy-3-O-benzyl-D-glucopyranose
  参考文献：
  名称：

  Studies Related to Synthesis of Glycophosphatidylinositol Membrane-Bound Protein Anchors. 6. Convergent Assembly of Subunits

  摘要：

  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.

  DOI：

  10.1021/ja00110a011

文献信息

• Synthesis of the essential core of the human glycosylphosphatidylinositol (GPI) anchor
  作者：Barbara Richichi、Lucio Luzzatto、Rosario Notaro、Giancarlo la Marca、Cristina Nativi

  DOI：10.1016/j.bioorg.2010.12.002

  日期：2011.4

  role of GPI anchors is of paramount importance; however, we are still far from fully understanding the structure–function relationship of these molecules. One major limiting factor has been the tiny quantities available from natural sources; obtaining homogeneous and well-defined GPI structures by synthesis, is both a challenge and an attractive goal. We report here the convergent synthesis of the essential

  GPI锚的生物学作用至关重要。然而，我们离完全了解这些分子的结构-功能关系还很远。一个主要的限制因素是可从自然资源中获得的微量产品。通过合成获得均质且定义明确的GPI结构，既是挑战，也是诱人的目标。我们在这里报告人类GPI锚点1的基本核心的收敛合成，利用共同的前体获得三糖供体2和新的保护基序列。首次制备的最终产品具有生物活性。
• Azido-Phenylselenylation of 3-<i>O</i>-Benzyl-2-Deoxy-5,6-<i>O</i>-Isopropylidene-D-<i>Arabino</i>-1,4-Anhydro-Hex-1-Enitol: Convenient Preparation of 2-Azido-2-Deoxy-D-Glucofurano-and Glucopyranoside Donors.
  作者：E. Chelain、S. Czernecki、M. Chmielewski、Z. Kaluza

  DOI：10.1080/07328309608005675

  日期：1996.7

  Azido-phenylselenylation of 3-O-benzyl-2-deoxy-5,6-O-isopropylidene-D-arabino-1, 4-anhydrohex-1-enitol (1) afforded an alpha/beta mixture of phenyl 2-azido-3-O-benzyl-2-deoxy-5,6-O-isopropylidene-1-seleno-D-glucofuranoside (2) together with a small amount of 3-O-benzyl-2-deoxy-5,6-O-isopropylidene-2-phenylseleno-D-glucofur?anosyl azide (3). Acetolysis of the mixture afforded 2-azido-2-deoxy-glucofuranosyl donor (4). Hydrolysis of the acetal group and of the selenoglycoside 2 followed by acetylation and removal of the anomeric acetate provide an efficient access to 5,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose (8), synthetic equivalent of D-glucosamine.