methyl 2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside | 1590421-89-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside
• 英文别名: ethyl 2-[(2R,3R,4S,5R,6S)-3-hydroxy-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]ethanesulfonate
• CAS: 1590421-89-8
• 化学式: C₂₄H₃₂O₈S
• 分子量: 480.579
• InChiKey: UDAOHHSEEVPZCW-SJSRKZJXSA-N

物化性质

• 沸点：
  640.3±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.33h， 生成 methyl [2-O-acetyl-3-O-methyl-α-L-idopyranosyl]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Large-scale synthesis of 6-deoxy-6-sulfonatomethyl glycosides and their application for novel synthesis of a heparinoid pentasaccharide trisulfonic acid of anticoagulant activity

  摘要：

  Multigram-scale syntheses of three 6-deoxy-6-sulfonatomethyl a-glucosides were accomplished via reactions of the corresponding primary triflate derivatives with the lithiated ethyl methanesulfonate. Chemoselective glycosylation reactions of different 6-C-sulfonatomethyl glucoside donors were studied. The sulfonic acid-containing building blocks were utilised in a novel [2+3] block synthesis of a trisulfonic acid isoster of the anticoagulant pentasaccharide idraparinux. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.02.012
• 作为产物：
  描述：

  methyl 2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-4-O-(2'-naphthyl)methyl-α-D-glucopyranoside 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以86%的产率得到methyl 2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Large-scale synthesis of 6-deoxy-6-sulfonatomethyl glycosides and their application for novel synthesis of a heparinoid pentasaccharide trisulfonic acid of anticoagulant activity

  摘要：

  Multigram-scale syntheses of three 6-deoxy-6-sulfonatomethyl a-glucosides were accomplished via reactions of the corresponding primary triflate derivatives with the lithiated ethyl methanesulfonate. Chemoselective glycosylation reactions of different 6-C-sulfonatomethyl glucoside donors were studied. The sulfonic acid-containing building blocks were utilised in a novel [2+3] block synthesis of a trisulfonic acid isoster of the anticoagulant pentasaccharide idraparinux. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.02.012

文献信息

• Synthesis and Cell Growth Inhibitory Activity of Six Non‐glycosaminoglycan‐Type Heparin‐Analogue Trisaccharides
  作者：Erika Lisztes、Erika Mező、Fruzsina Demeter、Lilla Horváth、Szilvia Bősze、Balázs István Tóth、Anikó Borbás、Mihály Herczeg

  DOI：10.1002/cmdc.202000917

  日期：2021.5.6

  lines. Two d‐glucuronate‐containing tetra‐O‐sulfated, partially methylated trisaccharides displayed remarkable and selective inhibitory effects on the growth of ovary carcinoma (A2780) and melanoma (WM35) cells. Methyl substituents on the glucuronide unit proved to be detrimental, whereas acetyl substituents were beneficial to the cytostatic activity of the sulfated derivatives.

  设计和合成具有高抗癌活性但无抗凝活性的肝素模拟物是药物化学中的一项重要任务。在此，我们提出了五种 Glc-GlcA-Glc 序列和一种 Glc-IdoA-Glc 序列非糖胺聚糖、肝素相关三糖的有效合成，具有各种硫酸化/磺酰化和甲基化模式。针对四种人类癌细胞系和两种非癌细胞系测试了这些化合物的细胞生长抑制作用。含两个d-葡萄糖醛酸的四-O-硫酸化、部分甲基化三糖对卵巢癌（A2780）和黑色素瘤（WM35）细胞的生长表现出显着的选择性抑制作用。葡萄糖醛酸苷单元上的甲基取代基被证明是有害的，而乙酰基取代基则有利于硫酸化衍生物的细胞抑制活性。
• Block Synthesis and Step-Growth Polymerization of C-6-Sulfonatomethyl-Containing Sulfated Malto-Oligosaccharides and Their Biological Profiling
  作者：Mihály Herczeg、Fruzsina Demeter、Tibor Nagy、Ágnes Rusznyák、Jan Hodek、Éva Sipos、István Lekli、Ferenc Fenyvesi、Jan Weber、Sándor Kéki、Anikó Borbás

  DOI：10.3390/ijms25010677

  日期：——

  derivatives up to dodecasaccharides were prepared by polymerization using different protecting groups, and the composition of the product mixtures was analyzed by MALDI-MS methods and size-exclusion chromatography. Synthesis of lower oligomers was also accomplished by stepwise and block synthetic methods, and then the oligosaccharide products were persulfated. The antiviral, anti-inflammatory and cell growth

  高度硫酸化的麦芽低聚物，类似于肝素和硫酸乙酰肝素，具有良好的抗病毒、抗转移、抗炎和细胞生长抑制作用。由于其广泛的生物活性和简单的结构，硫酸化麦芽低聚物衍生物具有巨大的治疗潜力，因此，开发其生产的有效合成方法至关重要。在这项工作中，通过不同的方法研究了在每个葡萄糖单元的C-6位上含有磺基甲基部分的α-(1→4)-连接的低聚葡萄糖苷的制备。使用不同的保护基通过聚合制备了麦芽低聚磺酸衍生物直至十二糖，并通过MALDI-MS方法和尺寸排阻色谱分析了产物混合物的组成。还通过逐步和嵌段合成方法完成了低级低聚物的合成，然后将低聚糖产物过硫酸化。通过体外试验测定了完全硫酸化麦芽低聚糖磺酸的抗病毒、抗炎和细胞生长抑制活性。四种测试的二糖和三糖磺酸可有效抑制 TNF-α 介导的炎症途径的激活，且未表现出细胞毒性。
• Large-scale synthesis of 6-deoxy-6-sulfonatomethyl glycosides and their application for novel synthesis of a heparinoid pentasaccharide trisulfonic acid of anticoagulant activity
  作者：Erika Mező、Mihály Herczeg、Dániel Eszenyi、Anikó Borbás

  DOI：10.1016/j.carres.2014.02.012

  日期：2014.3

  Multigram-scale syntheses of three 6-deoxy-6-sulfonatomethyl a-glucosides were accomplished via reactions of the corresponding primary triflate derivatives with the lithiated ethyl methanesulfonate. Chemoselective glycosylation reactions of different 6-C-sulfonatomethyl glucoside donors were studied. The sulfonic acid-containing building blocks were utilised in a novel [2+3] block synthesis of a trisulfonic acid isoster of the anticoagulant pentasaccharide idraparinux. (C) 2014 Elsevier Ltd. All rights reserved.