4-O-β-D-glucopyranosyloxybenzoic acid methyl ester | 75705-24-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-β-D-glucopyranosyloxybenzoic acid methyl ester
• 英文别名: Methyl 4-(I(2)-D-glucopyranosyloxy)benzoate；methyl 4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate
• CAS: 75705-24-7
• 化学式: C₁₄H₁₈O₈
• 分子量: 314.292
• InChiKey: IZEJPIRXGMAQFL-YGEZULPYSA-N

物化性质

• 沸点：
  550.9±50.0 °C(Predicted)
• 密度：
  1.465±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-O-β-D-glucopyranosyloxybenzoic acid methyl ester 在 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 14.0h， 生成 N'-(cyclohexylmethylene)-4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzohydrazide
  参考文献：
  名称：

  Synthesis and anti-tumor activity of glycosyl oxadiazoles derivatives

  摘要：

  A new series of glycosyl oxadiazoles compounds were synthesized and characterized through H-1 NMR, C-13 NMR, IR and HRMS. The anti-tumor activities for MDA-MB-231 of all these new compounds were screened in vitro by MTT assay. Due to the modification of gastrodin analogues, the anti-tumor activities of these 1,3,4-oxadiazoles derivatives were greatly improved. Six compounds (6c, 6d, 6i, 6j, 6k and 6l) displayed relatively higher MDA-MB-231 potency with IC50 values (0.89, 0.26, 1.35, 3.60, 0.95 and 1.08 mu M) compared with the reference medicine Rosiglitazone (5.23 mu M). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.042
• 作为产物：
  描述：

  对羟基苯甲酸甲酯 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-O-β-D-glucopyranosyloxybenzoic acid methyl ester
  参考文献：
  名称：

  氢键调控的超分子纳米结构及其对多价结合的影响

  摘要：

  在这里，我们描述了氢键调节的纳米结构，热力学和两个博拉两亲物NDI-1和NDI-2的多价结合，这两个疏水性萘二酰亚胺通过H键合基团与亲水性楔形连接，并且两个分子上都有一个葡萄糖部分武器。NDI-1和NDI-2的不同之处在于单个的H键合基团，即酰肼或酰胺，它们分别触发囊泡和圆柱形胶束的形成。尽管扩展的H键确保了头对头方向的堆叠并在两个系统中形成了一系列附加的葡萄糖部分，但自适应圆柱结构对伴刀豆球蛋白A（ConA）的囊泡表现出更高的多价结合能力。

  DOI：

  10.1002/anie.201812217

文献信息

• Synthesis of Oligomeric 4-(Glycosyloxy)benzoate Macrocyclic Glycosides
  作者：Yali Li、Jiansong Sun、Yanqing Gong、Biao Yu

  DOI：10.1021/jo200440r

  日期：2011.5.20

  Clemoarmanoside A and Clemahexapetoside A, two novel cyclic dimers of 4-(glycosyloxy)benzoates containing the unusual d-allopyranose as one of the sugar units, were synthesized for the first time. The convenient synthetic approach was adapted to the assembly of the symmetrical trimeric, tetrameric, and pentameric congeners. The synthesis clarified the discrepancy in the NMR data reported for the natural

  首次合成了Clemoarmanoside A和Clemahexapetoside A，这两种新型的4-（糖氧基氧基）苯甲酸酯的新型环状二聚体，其中含有不寻常的d-吡喃戊糖作为糖单元之一。方便的合成方法适用于对称三聚体，四聚体和五聚体同源物的组装。合成澄清了天然产物报道的NMR数据的差异。Clemahexapetoside A的X射线衍射分析表明，它采用了扶手椅构型，两个碳水化合物环分别为手臂，两个芳香环分别为椅背和座位。
• 一种糖基吲哚衍生物及其制备和应用
  申请人：杭州师范大学

  公开号：CN105017349B

  公开（公告）日：2018-04-20

  本发明公开了一种糖基吲哚衍生物及其制备和应用，所述糖基吲哚衍生物的结构如式（I）所示。所述糖基吲哚衍生物的制备方法包括：（1）式（II）所示的4‑吡喃葡萄糖苯甲酸甲酯和98％的水合肼在甲醇中回流反应，生成式（III）所示的4‑吡喃葡萄糖苯甲酰肼；（2）式（III）所示的4‑吡喃葡萄糖苯甲酰肼和式（IV）所示的吲哚‑3‑甲醛衍生物在乙醇中在醋酸的催化下进行反应，生成式（I）所示的糖基吲哚衍生物。本发明所述的糖基吲哚衍生物具有良好的抗肺肿瘤活性，可用于制备抗肺肿瘤药物。
• One undescribed glycoside benzofuran derivative and a new <i>p</i>-hydroxybenzoate glycoside from the leaves of <i>Illicium dunnianum</i> Tutcher
  作者：Xiao-qing He、Hai-bo Li、Ting Li、Xin-yin Chen、Zhen-zhong Wang、Xin-sheng Yao、Wei Xiao、Yang Yu

  DOI：10.1080/14786419.2023.2216348

  日期：——

  Abstract One undescribed benzofuran derivative (illiciumphenolicacid A, 1) and one new phenolic glycoside (illiciumphenolicacid B, 2), together with six known compounds (3–8) were isolated from the leaves of Illicium dunnianum Tutcher. Their structures were elucidated by detailed spectroscopic data (UV, IR, HR-ESI-MS, 1D and 2D NMR). In addition, we determined the α-glucosidase inhibitory activity

  摘要 从Illicium dunnianum Tutcher的叶子中分离出一种未描述的苯并呋喃衍生物（illiciumphenicacid A, 1）和一种新的酚苷（illiciumphenicacid B, 2）以及六种已知化合物（3–8 ）。通过详细的光谱数据（UV、IR、HR-ESI-MS、1D 和 2D NMR）阐明了它们的结构。此外，我们使用分光光度法测定了分离株的体外α-葡萄糖苷酶抑制活性。与阳性对照阿卡波糖 (IC 50 306.2 ± 4.1  μM ) 相比，化合物1–8具有中等的α电位-葡萄糖苷酶抑制活性，IC 50值在 380–655 μM范围内 。
• Synthetische Studien über die Beziehung zwischen chemischer Konstitution und Wirkung auf Mikroorganismen VIII. Mit F. L. Schweitzer: Glucoside der einfachen und chlorierten Paraoxybenzoesäure und ihrer Ester
  作者：Th. Sabalitschka

  DOI：10.1002/ardp.19292670903

  日期：——
• Isolation, identification and antioxidant activity of bound phenolic compounds present in rice bran
  作者：Wei Wang、Jia Guo、Junnan Zhang、Jie Peng、Tianxing Liu、Zhihong Xin

  DOI：10.1016/j.foodchem.2014.08.095

  日期：2015.3

  The bound phenolic compounds in rice bran were released and extracted with ethyl acetate based on alkaline digestion. An investigation of the chemical constituents of EtOAc extract has led to the isolation of a new compound, para-hydroxy methyl benzoate glucoside (8), together with nine known compounds, cycloeucalenol cis-ferulate (1), cycloeucalenol trans-ferulate (2), trans-ferulic acid (3), trans-ferulic acid methyl ester (4), cis-ferulic acid (5), cis-ferulic acid methyl ester (6), methyl caffeate (7), vanillic aldehyde (9) and para-hydroxy benzaldehyde (10). The structures of these compounds were determined using a combination of spectroscopic methods and chemical analysis. Among the compounds isolated, compound 3,5 and 7 exhibited strong DPPH and ABTS(+) radical scavenging activities, followed by compounds 4 and 6. Compound 1 and 2 showed potent DPPH and ABTS(+) radical scavenging activities, compound 8 displayed moderate antioxidant activity against ABTS(+) radical, whereas compound 9 and 10 showed weak antioxidant activity. (C) 2014 Elsevier Ltd. All rights reserved.