1-O-Allyl-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose | 144685-47-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 1-O-Allyl-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose
• 英文别名: (1R,2S,6S,9R)-4,4,11,11-tetramethyl-6-(prop-2-enoxymethyl)-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• CAS: 144685-47-2
• 化学式: C₁₅H₂₄O₆
• 分子量: 300.352
• InChiKey: AQNFFACRMFEPSM-FJJYHAOUSA-N

物化性质

• 沸点：
  367.9±37.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-O-Allyl-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  A Novel, Mild, and Practical Regeneration of Alcohols from their Allylic Ethers by NBS/H2O

  摘要：

  DOI：

  10.1021/jo00104a063
• 作为产物：
  描述：

  D-fructose 在 硫酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-O-Allyl-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose
  参考文献：
  名称：

  Inhibition of the d-fructose transporter protein GLUT5 by fused-ring glyco-1,3-oxazolidin-2-thiones and -oxazolidin-2-ones

  摘要：

  The glucose transporter 5 (GLUT5)-a specific D-fructose transporter-belongs to a family of facilitating sugar transporters recently enlarged by the human genome sequencing. Prompted by the need to develop specific photolabels of these isoforms, we have studied the interaction of conformationally locked D-fructose and L-sorbose derived 1,3-oxazolidin-2-thiones and 1,3-oxazolidin-2-ones to provide a rational basis for an interaction model. The inhibition properties of the D-fructose transporter GLUT5 by glyco-1,3-oxazolidin-2-thiones and glyco-1,3-oxazolidin-2-ones is now reported. In vitro, the fused-rings systems tested showed an efficient inhibition of GLUT5, thus bringing new insights on the interaction of D-fructose with GLUT5. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00007-7

文献信息

• Approaches to new water-soluble phosphines
  作者：Terence N. Mitchell、Kerstin Heesche-Wagner

  DOI：10.1016/0022-328x(92)85025-r

  日期：1992.9

  Approaches to water-soluble phosphines are described which involve conversion of ethylene glycol derivatives and sugar diacetonides into monoallyl ethers, and hydrophosphorylation of the latter. In the case of the sugars, water-solubility is conferred by a subsequent hydrolysis.

  描述了水溶性膦的方法，该方法涉及将乙二醇衍生物和糖二丙酮化物转化为单烯丙基醚，以及后者的磷酸化。在糖的情况下，通过随后的水解赋予水溶性。
• Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones
  作者：Xukai Zhou、Yan Xu、Guangbin Dong

  DOI：10.1021/jacs.1c09587

  日期：2021.12.8

  unique reaction pathway involving aromatization-driven C–C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C–C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes

  酮脱氢酰化为烯烃是在温和条件下实现的，它表现出独特的反应途径，包括芳构化驱动的 C-C 裂解以去除酰基部分，然后通过 Cu 介导的氧化消除在 α 和 β 碳之间形成烯烃。新采用的N'-甲基吡啶甲酰肼 (MPHA) 试剂是在室温下有效裂解酮 C-C 键的关键。生成具有广泛官能团耐受性的多种烷基和芳基取代的烯烃、二烯和特殊烯烃。还展示了该方法的战略应用。
• Synthesis of Glycoporphyrins by Cross-Metathesis Reactions
  作者：José Cavaleiro、Fernando de C. da Silva、Vitor Ferreira、Maria de Souza、Augusto Tomé、Maria Neves、Artur Silva

  DOI：10.1055/s-2008-1072718

  日期：2008.5

  An easy synthetic approach to glycoporphyrins from zinc(II)-2-vinyl-5,10,15,20-tetraphenylporphyrin or zinc(II)-protoporphyrin-IX dimethyl ester and O-allyl carbohydrate acetonides by cross-metathesis is reported.

  报告了一种通过交叉甲基化反应从锌(II)-2-乙烯基-5,10,15,20-四苯基卟啉或锌(II)-原卟啉-IX 二甲酯和 O-烯丙基碳水化合物丙酮合成糖卟啉的简便方法。
• Synthesis, characterization and X-ray structure of glycosyl-1,2-isoxazoles and glycosyl-1,2-isoxazolines prepared via 1,3-dipolar cycloaddition
  作者：Issam Gaamoussi、Ismail Fichtali、Abdeslem Ben Tama、El Mestafa El Hadrami、Donatella Armentano、Giovani De Munno、Miguel Julve、Salah-Eddine Stiriba

  DOI：10.1016/j.molstruc.2013.05.043

  日期：2013.9

  A convenient preparative method of a series of glycosyl-1,2-isoxazoles (6-11) and glycosyl-1,2-isoxazolines (15-20) by a simple and efficient 1,3-dipolar cycloaddition of a series of aryl nitrile oxide, generated in situ from aryl oximes (4-5), with a variety of O-propargyl glycosyles (1-3) or O-allyl glycosyles (12-14) respectively, is reported. The carbohydrate-containing 1,2-isoxazoles and 1,2-isoxazolines compounds were isolated in excellent yields (81-91%) and they were fully characterized by H-1, C-13 NMR and mass spectrometry. The relative stereochemistry of the glycosyl-1,2-isoxazole 10 was confirmed by single crystal X-ray analysis. The molecular structure of 10 confirms the retention of both, the anomeric stereochemistry of the D-fructose as well as the placement of the acetal groups. (c) 2013 Elsevier B.V. All rights reserved.
• Synthesis and evaluation of fructose analogues as inhibitors of the d -fructose transporter GLUT5
  作者：Arnaud Tatibouët、Jing Yang、Christophe Morin、Geoffrey D. Holman

  DOI：10.1016/s0968-0896(00)00108-5

  日期：2000.7

  We have examined the specificity and binding-site spatial requirements of the fructose transporter GLUT5. Interaction with a series of fructofuranosides and fructopyranosides suggests that both furanose and pyranose ring forms of D-fructose combine with GLUT5. The epimers of D-fructose all have low affinity for GLUT5 suggesting that the transporter requires all hydroxyls to be in the fructo-configuration. Similarly there is poor tolerance of all allyl derivatives of D-fructose except 6-O-allyl-D-fructo-furanose. Therefore, the C-6 position offers the most suitable position for development of affinity probes and labels for exploring GLUT5 biochemistry. (C) 2000 Elsevier Science Ltd. All rights reserved.