1,2,3,4,6-penta-O-butyryl-β-D-glucopyranose | 569660-14-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 1,2,3,4,6-penta-O-butyryl-β-D-glucopyranose
• 英文别名: (2R,3R,4S,5R,6R)-6-((butyryloxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetrabutyrate；[(2R,3R,4S,5R,6S)-3,4,5,6-tetra(butanoyloxy)oxan-2-yl]methyl butanoate
• CAS: 569660-14-6
• 化学式: C₂₆H₄₂O₁₁
• 分子量: 530.613
• InChiKey: URBLVNWOCAGFPV-MGHSTNRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  37
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,2,3,4,6-penta-O-butyryl-β-D-glucopyranose 在 三乙烯二胺 、 水 、 甲胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 生成 (2S,3R,4S,5R,6R)-2-(2-((benzyloxy)carbonyl)-4-nitrophenoxy)-6-((butyryloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tributyrate
  参考文献：
  名称：

  [EN] ACYLATED ACTIVE AGENTS AND METHODS OF THEIR USE FOR THE TREATMENT OF AUTOIMMUNE DISORDERS
  [FR] AGENTS ACTIFS ACYLÉS ET LEURS PROCÉDÉS D'UTILISATION POUR LE TRAITEMENT DE TROUBLES AUTO-IMMUNS

  摘要：

  公开号：

  WO2019236772A8
• 作为产物：
  描述：

  丁酸酐 、 D-葡萄糖 在 吡啶 作用下， 反应 16.0h， 以60%的产率得到
  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

• Active agents and methods of their use for the treatment of metabolic disorders and nonalcoholic fatty liver disease
  申请人：Flagship Pioneering Innovations V, Inc.

  公开号：US10953027B2

  公开（公告）日：2021-03-23

  Disclosed herein are active agents, compositions containing them, unit dosage forms containing them, and methods of their use, e.g., for treating a metabolic disorder or nonalcoholic fatty liver disease or for modulating a metabolic marker or nonalcoholic fatty liver disease marker.

  本文公开了活性剂、含有活性剂的组合物、含有活性剂的单位剂型以及活性剂的使用方法，例如用于治疗代谢紊乱或非酒精性脂肪肝或调节代谢标志物或非酒精性脂肪肝标志物。
• NOVEL CARBOHYDRATE ESTERS AND POLYOL ESTERS AS PLASTICIZERS FOR POLYMERS, COMPOSITIONS AND ARTICLES INCLUDING SUCH PLASTICIZERS AND METHODS OF USING THE SAME
  申请人：EASTMAN CHEMICAL COMPANY

  公开号：EP1465944B1

  公开（公告）日：2015-02-25
• ACTIVE AGENTS AND METHODS OF THEIR USE FOR THE TREATMENT OF METABOLIC DISORDERS AND NONALCOHOLIC FATTY LIVER DISEASE
  申请人：Flagship Pioneering Innovations V, Inc.

  公开号：US20200197428A1

  公开（公告）日：2020-06-25

  Disclosed herein are active agents, compositions containing them, unit dosage forms containing them, and methods of their use, e.g., for treating a metabolic disorder or nonalcoholic fatty liver disease or for modulating a metabolic marker or nonalcoholic fatty liver disease marker.
• [EN] ACYLATED ACTIVE AGENTS AND METHODS OF THEIR USE FOR THE TREATMENT OF AUTOIMMUNE DISORDERS<br/>[FR] AGENTS ACTIFS ACYLÉS ET LEURS PROCÉDÉS D'UTILISATION POUR LE TRAITEMENT DE TROUBLES AUTO-IMMUNS
  申请人：FLAGSHIP PIONEERING INNOVATIONS V INC

  公开号：WO2019236772A8

  公开（公告）日：2020-07-02
• 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.