4-phenyl-1-(2',3',4',6'-tetra-O-butanoyl-β-D-glucopyranosyl)-1H-1,2,3-triazole | 1417909-39-7

• 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: 4-phenyl-1-(2',3',4',6'-tetra-O-butanoyl-β-D-glucopyranosyl)-1H-1,2,3-triazole
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-tri(butanoyloxy)-6-(4-phenyltriazol-1-yl)oxan-2-yl]methyl butanoate
• CAS: 1417909-39-7
• 化学式: C₃₀H₄₁N₃O₉
• 分子量: 587.67
• InChiKey: JZQVFOIWCBFNGG-NRCRZUOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  42
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  D-glucopyranosyl azide 在 吡啶 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 乙醇 、 水 为溶剂， 反应 4.5h， 生成 4-phenyl-1-(2',3',4',6'-tetra-O-butanoyl-β-D-glucopyranosyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Synthesis of acylated glycoconjugates as templates to investigate in vitro biopharmaceutical properties

  摘要：

  A series of novel glycopyranosyl azides were synthesised wherein the carbohydrate moiety was peracylated with four acetyl, propionyl, butanoyl, pentanoyl (valeryl) or 3-methylbutanoyl (isovaleryl) ester linked groups. A panel of glycoconjugates was synthesised from these glycopyranosyl azides using copper-catalysed azide-alkyne cycloaddition. The in vitro metabolic stability, plasma stability and plasma protein binding was then measured to establish the impact of the different acyl group when presented on a common scaffold. The acetyl, propionyl and butanoyl esters exhibited metabolism consistent with esterase processing, and various mono-, di- and tri-acylated hydrolysis products as well as the fully hydrolysed compound were detected. In contrast, the pentanoyl and 3-methylbutanoyl esters were stable. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.056

文献信息

• Synthesis of acylated glycoconjugates as templates to investigate in vitro biopharmaceutical properties
  作者：Cindy J. Carroux、Janina Moeker、Josephine Motte、Marie Lopez、Laurent F. Bornaghi、Kasiram Katneni、Eileen Ryan、Julia Morizzi、David M. Shackleford、Susan A. Charman、Sally-Ann Poulsen

  DOI：10.1016/j.bmcl.2012.11.056

  日期：2013.1

  A series of novel glycopyranosyl azides were synthesised wherein the carbohydrate moiety was peracylated with four acetyl, propionyl, butanoyl, pentanoyl (valeryl) or 3-methylbutanoyl (isovaleryl) ester linked groups. A panel of glycoconjugates was synthesised from these glycopyranosyl azides using copper-catalysed azide-alkyne cycloaddition. The in vitro metabolic stability, plasma stability and plasma protein binding was then measured to establish the impact of the different acyl group when presented on a common scaffold. The acetyl, propionyl and butanoyl esters exhibited metabolism consistent with esterase processing, and various mono-, di- and tri-acylated hydrolysis products as well as the fully hydrolysed compound were detected. In contrast, the pentanoyl and 3-methylbutanoyl esters were stable. (c) 2012 Elsevier Ltd. All rights reserved.