1,2,3,4,6-penta-O-propionyl-D-glucopyranose | 400083-02-5

• 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: 1,2,3,4,6-penta-O-propionyl-D-glucopyranose
• 英文别名: [(2R,3R,4S,5R)-3,4,5,6-tetra(propanoyloxy)oxan-2-yl]methyl propanoate
• CAS: 400083-02-5
• 化学式: C₂₁H₃₂O₁₁
• 分子量: 460.478
• InChiKey: QZJNZSMFMAIQHD-WIJDAZEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  32
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 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-propionyl-D-glucopyranose 在 copper(ll) sulfate pentahydrate 、 叠氮基三甲基硅烷 、 四氯化锡 、 sodium ascorbate 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 20.5h， 生成 4-phenyl-1-(2',3',4',6'-tetra-O-propionyl-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
• 作为产物：
  描述：

  D-葡萄糖 、 丙酸酐 在 indium(III) triflate 作用下， 反应 2.0h， 以90%的产率得到1,2,3,4,6-penta-O-propionyl-D-glucopyranose
  参考文献：
  名称：

  三氟甲磺酸铟（III）：糖反应的高效催化剂[1]

  摘要：

  已经发现三氟甲磺酸铟（III）在催化各种碳水化合物及其衍生物的酰基转移反应中非常有效。使用In（OTf）3在Ac2O中（纯净）可以对某些糖的苄基醚/异亚丙基缩醛进行选择性乙酰水解。在In（OTf）3存在下2-脱氧-2-邻苯二甲酰亚胺基-D-葡萄糖的全-O-乙酸酯与苄硫醇的反应导致高产率地形成相应的硫代糖苷。在In（OTf）3的存在下，也非常有效地实现了各种碳水化合物的异亚丙基和亚苄基缩醛的轻松形成和水解。结果表明，In（OTf）3在合成碳水化合物化学中具有广阔的前景。

  DOI：

  10.1080/07328300802458970

文献信息

• Design, Synthesis, and Biological Evaluation of Novel Carbohydrate-Based Sulfamates as Carbonic Anhydrase Inhibitors
  作者：Marie Lopez、Jonathan Trajkovic、Laurent F. Bornaghi、Alessio Innocenti、Daniela Vullo、Claudiu T. Supuran、Sally-Ann Poulsen

  DOI：10.1021/jm101525j

  日期：2011.3.10

  Carbonic anhydrases (CAs) IX and XII are enzymes with newly validated potential for the development of personalized, first-in-class cancer chemotherapies. Here we present the design and synthesis of novel carbohydrate-based CA inhibitors, several of which were very efficient inhibitors (K-i < 10 nM) with good selectivity for cancer-associated CA isozymes over off-target CA isozymes. All inhibitors comprised a carbohydrate core with one hydroxyl group derivatized as a sulfamate. Five different carbohydrates were chosen to present a selection of molecular shapes with subtle stereochernical differences to the CA enzymes active site. Variable modifications of the remaining sugar hydroxyl groups were incorporated to provide an incremental coverage of chemical property parameters that are associated with biopharmaceutical performance. All sulfamate inhibitors displayed ligand efficiencies that are consistent with those reported for good drug lead candidates.
• Indium(III) Triflate: A Highly Efficient Catalyst for Reactions of Sugars^[1]
  作者：Santosh Kumar Giri、Monika Verma、K. P. Ravindranathan Kartha

  DOI：10.1080/07328300802458970

  日期：2008.12.11

  Indium(III) trifluoromethanesulfonate has been found to be extremely efficient in catalyzing acyl transfer reactions of various carbohydrates and their derivatives. Selective acetolyses of certain benzyl ethers/isopropylidene acetals of sugars have been possible using In(OTf)3 in Ac2O (neat). Reaction of the per-O-acetate of 2-deoxy-2-phthalimido-D-glucose with benzyl mercaptan in the presence of In(OTf)3

  已经发现三氟甲磺酸铟（III）在催化各种碳水化合物及其衍生物的酰基转移反应中非常有效。使用In（OTf）3在Ac2O中（纯净）可以对某些糖的苄基醚/异亚丙基缩醛进行选择性乙酰水解。在In（OTf）3存在下2-脱氧-2-邻苯二甲酰亚胺基-D-葡萄糖的全-O-乙酸酯与苄硫醇的反应导致高产率地形成相应的硫代糖苷。在In（OTf）3的存在下，也非常有效地实现了各种碳水化合物的异亚丙基和亚苄基缩醛的轻松形成和水解。结果表明，In（OTf）3在合成碳水化合物化学中具有广阔的前景。
• 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.