1,2,3,4-tetra-O-acetyl-β-D-glucopyranosiduronic acid allyl ester | 725738-59-0

• 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-tetra-O-acetyl-β-D-glucopyranosiduronic acid allyl ester
• 英文别名: allyl 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronate；allyl 3,4,5,6-tetra(acetyloxy)tetrahydro-2H-2-pyrancarboxylate；I(2)-D-Glucopyranuronic acid, 2-propen-1-yl ester, 1,2,3,4-tetraacetate；prop-2-enyl (2S,3S,4S,5R,6S)-3,4,5,6-tetraacetyloxyoxane-2-carboxylate
• CAS: 725738-59-0
• 化学式: C₁₇H₂₂O₁₁
• 分子量: 402.355
• InChiKey: AGQJGYTZBDJCEL-NBFUAULTSA-N

物化性质

• 熔点：
  95-97 °C
• 沸点：
  446.9±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 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-tetra-O-acetyl-β-D-glucopyranosiduronic acid allyl ester 在 四氢吡咯 、 四(三苯基膦)钯 、 草酰氯 、 叠氮基三甲基硅烷 、 四氯化锡 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 Acetic acid (2S,3S,4S,5R,6R)-4,5-diacetoxy-6-azido-2-chlorocarbonyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis and X-ray single crystal structure of a bivalent glycocluster

  摘要：

  一种含有芳香族酰胺的双价糖簇的晶体结构显示，次级酰胺的烷基化改变了酰胺的构型，从而改变了碳水化合物的呈现。这还促进了非共价相互作用（叠氮–叠氮、羰基–吡喃糖和芳香族–吡喃糖），从而增强了碳水化合物之间的堆积。

  DOI：

  10.1039/b313934d
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic acid 在 吡啶 、 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 1,2,3,4-tetra-O-acetyl-β-D-glucopyranosiduronic acid allyl ester
  参考文献：
  名称：

  Synthesis and X-ray single crystal structure of a bivalent glycocluster

  摘要：

  一种含有芳香族酰胺的双价糖簇的晶体结构显示，次级酰胺的烷基化改变了酰胺的构型，从而改变了碳水化合物的呈现。这还促进了非共价相互作用（叠氮–叠氮、羰基–吡喃糖和芳香族–吡喃糖），从而增强了碳水化合物之间的堆积。

  DOI：

  10.1039/b313934d

文献信息

• Glycosidation–Anomerisation Reactions of 6,1-Anhydroglucopyranuronic Acid and Anomerisation of β-D-Glucopyranosiduronic Acids Promoted by SnCl4
  作者：Colin O'Brien、Monika Poláková、Nigel Pitt、Manuela Tosin、Paul V. Murphy

  DOI：10.1002/chem.200601111

  日期：2007.1.12

  onic acids was found to be faster, in some cases, than anomerisation of related beta-D-glucopyranosiduronic acid esters and beta-D-glucopyranoside derivatives and the rates are dependent on the structure of the aglycon. Moreover, the rates of anomerisation of beta-D-glucopyranuronic acid derivatives can be qualitatively correlated with rates of hydrolysis of beta-D-glucopyranosiduronic acids. Mechanistic

  氯化锡（IV）催化的甲硅烷基化亲核试剂与6,1-脱水葡萄糖基吡喃糖醛酸（葡萄糖醛酸6,1-内酯）的反应提供了1,2-反式或1,2-顺式（脱氧）糖苷，具体取决于供体结构。对于供体与2-酰基和2-脱氧供体的反应，获得了α-糖苷，而2-脱氧-2-碘的供体给出了β-糖苷。实验证据表明，当1,2-顺式糖苷形成时，由SnCl（4）催化的最初形成的1,2-反式糖苷的异构化是可能的。在某些情况下，发现β-D-吡喃葡萄糖苷神经酸酯的异构化比相关的β-D-吡喃葡萄糖苷神经酸酯和β-D-吡喃葡萄糖苷衍生物的异构化更快，并且速率取决于糖苷配基的结构。而且，β-D-吡喃葡萄糖醛酸衍生物的异构化速率可以与β-D-吡喃葡萄糖醛糖醛酸的水解速率定性相关。考虑了反应的机械可能性。
• Synthesis and Structural Analysis of the Anilides of Glucuronic Acid and Orientation of the Groups on the Carbohydrate Scaffolding
  作者：Manuela Tosin、Colin O'Brien、Geraldine M. Fitzpatrick、Helge Müller-Bunz、W. Kenneth Glass、Paul V. Murphy

  DOI：10.1021/jo0501994

  日期：2005.5.1

  synthesis of anilides derived from glucuronic acid is described. Secondary anilides had a Z configuration in the solid state and showed intramolecular and intermolecular hydrogen bonding. However, on the basis of NMR and IR studies, there was generally no evidence for the same hydrogen bonding in solution. Tertiary anilides showed a strong preference for the E configuration on the basis of NOE studies and molecular

  描述了衍生自葡糖醛酸的酸酐的合成。仲酸酐在固态具有Z构型，并显示出分子内和分子间的氢键。但是，基于NMR和IR研究，通常没有证据表明溶液中存在相同的氢键。在NOE研究和分子力学计算的基础上，叔酸酐显示出对E构型的强烈偏好。仲酸酐的烷基化引起构型转换，该构型转换改变了芳族基团相对于吡喃糖的取向，这与碳水化合物支架上药效基团的呈递或取向有关。
• Esters Of Glucuronide Prodrugs Of Anthracyclines And Method Of Preparation And Use In Tumor-Selective Chemotherapy
  申请人：Aben Rene Wilhelmus Marie

  公开号：US20090227617A1

  公开（公告）日：2009-09-10

  The invention relates to novel esters and in particular to some novel esters of glucuronide prodrugs of anthracyclines having tunable water-solubility, their synthesis and use in tumor-selective chemotherapy. It appeared that in the final step in the synthesis of these prodrugs, i.e. the coupling of the glucuronide spacer moiety to the parent drug molecule, protection of the sugar hydroxyls is, surprisingly, no longer required. A process for the preparation of these unprotected sugar spacer moieties is also disclosed.

  该发明涉及新型酯类化合物，特别是一些新型葡萄糖醛酸盐前药的酯类化合物，其具有可调节的水溶性，以及它们在肿瘤选择性化疗中的合成和应用。在这些前药的合成的最后一步中，即将葡萄糖醛酸盐间隔基与母药分子偶联时，令人惊讶的是，不再需要保护糖羟基。还公开了一种制备这些未保护糖间隔基的过程。
• Glucuronic acid as a helix-inducing linker in short peptides
  作者：Chongyang Wu、Huy N. Hoang、Ligong Liu、David P. Fairlie

  DOI：10.1039/c7cc09785a

  日期：——

  A new strategy is demonstrated for making peptides helical, using a carbohydrate to bridge between sidechains at each end of a pentapeptide. CD and NMR spectra establish that both an α-helix and a 310-helix structure can form depending upon the bridge.

  使用碳水化合物在五肽各末端的侧链之间架桥的新方法已被证明可以使肽呈螺旋状。CD和NMR谱确定，取决于桥，可以形成α-螺旋和3 10-螺旋结构。
• Glycosylation and functionalization of native amino acids with azido uronic acids
  作者：Consulato J. Cara、Danielle Skropeta

  DOI：10.1016/j.tet.2015.10.001

  日期：2015.12

  Bifunctional, acetyl-protected, azido glucuronic and galacturonic acid derivatives were coupled via the carboxylic acid moiety to amine- and hydroxyl-containing side chains of the natural amino acids lysine and serine or via the N-terminus of the amino acids leucine, methionine and glutamine. The glycosylated amino acids were then functionalized via the free azido moiety to produce the corresponding anomeric triazole derivatives. This approach enables the dual glycosylation and functionalization of a range of native amino acids in high yields. Crown Copyright (C) 2015 Published by Elsevier Ltd. All rights reserved.