benzyl 6-O-trityl-2,3,4-tri-O-benzyl-D-glucopyranoside | 953812-26-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: benzyl 6-O-trityl-2,3,4-tri-O-benzyl-D-glucopyranoside
• 英文别名: (3R,4S,5R,6R)-2,3,4,5-tetrakis(benzyloxy)-6-((trityloxy)methyl)tetrahydro-2H-pyran；1,2,3,4-tetra-O-benzyl-6-O-trityl-D-glucopyranose
• CAS: 953812-26-5
• 化学式: C₅₃H₅₀O₆
• 分子量: 782.976
• InChiKey: GWEFKLSXFOMSCJ-HQCSBRPFSA-N

物化性质

• 沸点：
  829.9±65.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.69
• 重原子数：
  59.0
• 可旋转键数：
  18.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  benzyl 6-O-trityl-2,3,4-tri-O-benzyl-D-glucopyranoside 在 potassium dichromate 、 草酰氯 、 硫酸 、 氢溴酸 、 溶剂黄146 、 N,N-二甲基甲酰胺 作用下， 以 丙酮 为溶剂， 反应 4.57h， 生成
  参考文献：
  名称：

  Glycosylated Platinum(IV) Complexes as Substrates for Glucose Transporters (GLUTs) and Organic Cation Transporters (OCTs) Exhibited Cancer Targeting and Human Serum Albumin Binding Properties for Drug Delivery

  摘要：

  Glycosylated platinum(IV) complexes were synthesized as substrates for GLUTs and OCTs for the first time, and the cytotoxicity and detailed mechanism were determined in vitro and in vivo. Galactoside Pt(IV), glucoside Pt(IV), and mannoside Pt(W) were highly cytotoxic and showed specific cancer-targeting properties in vitro and in vivo. Glycosylated platinum(W) complexes 5, 6, 7, and 8 (IC50 0.24-3.97 mu M) had better antitumor activity of nearly 166-fold higher than the positive controls cisplatin (1a), oxaliplatin (3a), and satraplatin (5a). The presence of a hexadecanoic chain allowed binding with human serum albumin (HSA) for drug delivery, which not only enhanced the stability of the inert platinum(IV) prodrugs but also decreased their reduction by reductants present in human whole blood. Their preferential accumulation in cancer cells compared to noncancerous cells (293T and 3T3 cells) suggested that they were potentially safe for clinical therapeutic use.

  DOI：

  10.1021/acs.jmedchem.7b00433
• 作为产物：
  描述：

  苯甲醇 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 、 乙酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.33h， 生成 benzyl 6-O-trityl-2,3,4-tri-O-benzyl-D-glucopyranoside
  参考文献：
  名称：

  Glycosylated Platinum(IV) Complexes as Substrates for Glucose Transporters (GLUTs) and Organic Cation Transporters (OCTs) Exhibited Cancer Targeting and Human Serum Albumin Binding Properties for Drug Delivery

  摘要：

  Glycosylated platinum(IV) complexes were synthesized as substrates for GLUTs and OCTs for the first time, and the cytotoxicity and detailed mechanism were determined in vitro and in vivo. Galactoside Pt(IV), glucoside Pt(IV), and mannoside Pt(W) were highly cytotoxic and showed specific cancer-targeting properties in vitro and in vivo. Glycosylated platinum(W) complexes 5, 6, 7, and 8 (IC50 0.24-3.97 mu M) had better antitumor activity of nearly 166-fold higher than the positive controls cisplatin (1a), oxaliplatin (3a), and satraplatin (5a). The presence of a hexadecanoic chain allowed binding with human serum albumin (HSA) for drug delivery, which not only enhanced the stability of the inert platinum(IV) prodrugs but also decreased their reduction by reductants present in human whole blood. Their preferential accumulation in cancer cells compared to noncancerous cells (293T and 3T3 cells) suggested that they were potentially safe for clinical therapeutic use.

  DOI：

  10.1021/acs.jmedchem.7b00433

文献信息

• [EN] INHIBITORS OF MALARIAL AND PLASMODIUM FALCIPARUM HEXOSE TRANSPORTER AND USES THEREOF<br/>[FR] INHIBITEURS DU TRANSPORTEUR D'HEXOSE DE LA MALARIA ET DE PLASMODIUM FALCIPARUM ET LEURS UTILISATIONS
  申请人：UNIV TSINGHUA

  公开号：WO2021155748A1

  公开（公告）日：2021-08-12

  Provided are molecules capable of binding to binding pockets of Plasmodium falciparum hexose transporter (PfHT) or analogs thereof and complexes comprising the same. Also provided herein are inhibitors of PfHT, pharmaceutical compositions comprising the inhibitors, and methods of using the inhibitors or the pharmaceutical compositions in the treatment of diseases associated with Plasmodium or PfHT or the killing or inhibiting the growth of Plasmodium. Provided are a set of structure coordinates of such binding pockets and method of using the set of structure coordinates to screen for and design compounds that are capable of binding to PfHT or analogs thereof.

  提供了能够结合到疟原虫己糖转运蛋白（PfHT）或其类似物的结合口袋的分子，以及包含这些分子的复合物。此外，还提供了PfHT的抑制剂，包含这些抑制剂的药物组合物，以及在治疗与疟原虫或PfHT相关的疾病或杀死或抑制疟原虫生长中使用这些抑制剂或药物组合物的方法。提供了这些结合口袋的结构坐标集合，并提供了使用这些结构坐标集合来筛选和设计能够结合到PfHT或其类似物的化合物的方法。
• Regioselective Anomeric <i>O</i> ‐Benzyl Deprotection in Carbohydrates
  作者：Perali Ramu Sridhar、Bandi Anjaneyulu、Boddu Umamaheswara Rao

  DOI：10.1002/ejoc.202101033

  日期：2021.11.8

  A simple and highly regioselective hydrogenolysis of the anomeric benzyl group is reported. The generality and the scope of the reaction were evaluated by applying it to a number of diversly protected benzyl monosaccharides and disaccharides that lead to the formation of the corresponding hemiacetals in good yield.

  报道了异头苄基的简单且高度区域选择性的氢解。反应的一般性和范围是通过将其应用于许多不同保护的苄基单糖和二糖来评估的，这些苄基单糖和二糖导致以良好的产率形成相应的半缩醛。
• Phosphonate and α-Fluorophosphonate Analogues of <scp>d</scp>-Glucose 6-Phosphate as Active-Site Probes of 1<scp>l</scp>-<i>myo</i>-Inositol 1-Phosphate Synthase
  作者：Josseline S. Ramos-Figueroa、David R. J. Palmer

  DOI：10.1021/acs.biochem.2c00064

  日期：2022.5.17

  amino acid residues in the active site. Crystal structures of mIPS in the ternary complex with substrate analogues and NAD(H) show different ligand orientations. We therefore proposed to use isosteric and isoelectronic analogues of G6P to probe the active site. Here, we report the synthesis of the methylenephosphonate, difluoromethylenephosphonate, and (R)- and (S)-monofluoromethylenephosphonate analogues

  肌醇(mI)的生物合成是所有生命王国中许多生物体功能的核心。该途径的第一步和限速步骤由 1 l-肌醇1-磷酸合酶 (mIPS) 催化，它将d-葡萄糖 6-磷酸 (G6P) 转化为 1 l-肌醇1-磷酸 ( mI1P ）。广泛的研究表明，这种反应是通过逐步的 NAD +-依赖性氧化还原醛醇环化机制产生对映体纯的mI1P。尽管已经阐明了该机制的立体化学性质，但对活性位点中氨基酸残基的重要性缺乏了解。具有底物类似物和 NAD(H) 的三元复合物中 mIPS 的晶体结构显示出不同的配体取向。因此，我们建议使用 G6P 的等排和等电子类似物来探测活性位点。在这里，我们报告了 G6P 的亚甲基膦酸酯、二氟亚甲基膦酸酯和 ( R )- 和 ( S )-单氟亚甲基膦酸酯类似物的合成及其作为 mIPS 活性抑制剂的评估。而 CH 2和 CF 2类似物是通过对先前描述的途径进行轻微修改而产生的，CHF 类似物
• WO2007/54977
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of cyclophospho-glucoses and glucitols
  作者：E.J. Amigues、M.L. Greenberg、S. Ju、Y. Chen、M.E. Migaud

  DOI：10.1016/j.tet.2007.07.027

  日期：2007.10

  The syntheses of cyclophosphodiesters of 5-C-(hydroxymethyl)-hexoses and hexitols and of 6-C-(hydroxymethyl)-hexoses are reported, along with that of 6-deoxy-gluco-heptose 7-phosphate. These compounds proved to be reasonable substrate mimics and show inhibitory activity against human D-myo-inositol 3-phosphate synthase. (c) 2007 Elsevier Ltd. All rights reserved.