benzyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside | 74590-46-8

• 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: benzyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside
• 英文别名: benzylthio-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside；(2R,3R,4S,5S,6R)-2-(Acetoxymethyl)-6-(benzylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate；[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-benzylsulfanyloxan-2-yl]methyl acetate
• CAS: 74590-46-8
• 化学式: C₂₁H₂₆O₉S
• 分子量: 454.498
• InChiKey: UVVCYZREUQWNFB-CRSSMBPESA-N

物化性质

• 熔点：
  139-140 °C
• 沸点：
  526.0±50.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 在 HOF* CH₃CN 作用下， 以 氯仿 为溶剂， 反应 0.03h， 以92%的产率得到benzyl 2,3,4,6-tetra-O-acetyl-1-sulfonyl-α-D-mannopyranoside
  参考文献：
  名称：

  Application of HOF·CH3CN to the synthesis of glycosyl sulfones

  摘要：

  A fast, complete and clean conversion of thioglycosides into glycosyl sull'ones under mild acidic conditions is described, using the HOF center dot CH3CN complex at room temperature. This methodology affords glycosyl sull'ones in high yields and in excellent purity. (c) 2008 Elsevier Ltd. All rights reserved,

  DOI：

  10.1016/j.tet.2008.05.033
• 作为产物：
  描述：

  2-S-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-thiopseudourea hydrobromide 在 potassium disulphite 、 potassium carbonate 作用下， 以 氯仿 、 水 、 丙酮 为溶剂， 反应 1.5h， 生成 benzyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  胰岛素样和胰岛素拮抗的碳水化合物衍生物。芳基和芳烷基D-甘露糖吡喃糖苷和1-硫代-D-甘露糖吡喃糖苷的合成。

  摘要：

  合成了许多新颖的芳基和芳烷基D-甘露糖吡喃糖苷和1-硫代-D-甘露糖吡喃糖苷，用于评估胰岛素样和胰岛素拮抗性质。通过Helferich和Schmitz-Hillebrecht的通用方法制备取代的苯基α-D-甘露糖吡喃糖苷，通过对应于芳族糖苷的迈克尔合成的方法制备取代的苯基1-硫代α-D-甘露糖吡喃糖苷，以及芳烷基。通过2,3,4,6-四-O-乙酰基-1-硫代-α-D-甘露吡喃糖的芳烷基化作用制备1-硫代-α-D-甘露吡喃糖苷（15），然后进行O-脱乙酰化。通过将2-O-乙酰基-α-D反应的产物2-S-（四-O-乙酰基-α-D-甘露吡喃糖基）-2-thiopseudourea氢溴酸盐中的mid基进行碱性裂解，得到化合物15。 -甘露糖基溴与硫脲。苄基1-硫代-β-D-甘露吡喃糖苷

  DOI：

  10.1016/s0008-6215(00)85657-8

文献信息

• A New Route toexo-Glycals Using the Ramberg−Bäcklund Rearrangement
  作者：Frank K. Griffin、Duncan E. Paterson、Paul V. Murphy、Richard J. K. Taylor

  DOI：10.1002/1099-0690(200204)2002:7<1305::aid-ejoc1305>3.0.co;2-0

  日期：2002.4

  A new route to exo-glycals 4 is described in which glycosyl sulfones 3 are subjected to the Meyers variant of the Ramberg−Bäcklund rearrangement. The conversion of sulfones derived from glucose, galactose, mannose, cellobiose, and ribose into di-, tri-, and tetra-substituted alkenes is reported. Preliminary mechanistic studies of this process are also described. (© Wiley-VCH Verlag GmbH, 69451 Weinheim

  描述了一种通往外糖4的新途径，其中糖基砜3经历了Ramberg-Bäcklund重排的Meyers变体。据报道，衍生自葡萄糖，半乳糖，甘露糖，纤维二糖和核糖的砜转化为二，三和四取代的烯烃。还介绍了此过程的初步机理研究。（©Wiley-VCH Verlag GmbH，69451 Weinheim，Germany，2002）
• Modified One‐Pot Protocol for the Preparation of Thioglycosides from Unprotected Aldoses via <i>S</i>‐Glycosyl Isothiouronium Salts
  作者：Pallavi Tiwari、Geetanjali Agnihotri、Anup Kumar Misra

  DOI：10.1080/07328300500256775

  日期：2005.9.1

  An efficient one‐pot protocol for the direct preparation of thioglycosides starting from unprotected reducing sugars via S‐glycosyl isothiouronium salts is reported. In this one‐pot methodology, BF3 · OEt2 has been used as a general catalyst for both per‐O‐acetylation of sugars and conversion of sugar per‐O‐acetates into S‐glycosyl isothiouronium salts, which was allowed to react with alkylating agents

  据报道，一种有效的一锅法方案可直接从未保护的还原糖开始，通过S-糖基异硫脲盐直接制备硫糖苷。在这种一锅法中，BF3·OEt2已被用作糖的全O-乙酰化和糖的过O-乙酸转化为S-糖基异硫脲盐的通用催化剂，该盐可与烷化剂反应在碱的存在下以优异的产率提供硫代糖苷。* CDRI通讯号 6767.作者对这项工作做出了同等的贡献。
• Synthesis of thio- and selenoglycosides by cleavage of dichalconides in the presence of zinc/zinc chloride and reaction with glycosyl bromides
  作者：Chinmoy Mukherjee、Pallavi Tiwari、Anup Kumar Misra

  DOI：10.1016/j.tetlet.2005.11.074

  日期：2006.1

  A convenient odorless methodology has been devised for the preparation of 1,2-trans-thio- and selenoglycosides through zinc-mediated cleavage of disulfides and diselenides and reaction of the thiolate and selenides formed in situ with glycosyl bromides. The yields were excellent in all cases.

  已经设计了一种方便的无味方法，用于通过锌介导的二硫化物和二硒化物的裂解以及原位形成的硫醇盐和硒化物与糖基溴化物的反应来制备1,2-反式-硫代和硒代糖苷。在所有情况下，收率都非常好。
• Design, synthesis, biological evaluation and docking study of some new aryl and heteroaryl thiomannosides as FimH antagonists
  作者：Anber F. Mohammed、Shimaa A. Othman、Ola F. Abou-Ghadir、Ahmed A. Kotb、Yaser A. Mostafa、Mohamed A. El-Mokhtar、Hajjaj H.M. Abdu-Allah

  DOI：10.1016/j.bioorg.2024.107258

  日期：2024.4

  discovery and optimization of small molecule aryl mannoside FimH antagonists. These antagonists retain key specific interactions of the mannose scaffolds with the FimH carbohydrate recognition domains. Thiomannosides are attractive and stable scaffolds, and this work reports the synthesis of some of their new aryl and heteroaryl derivatives as FimH antagonists. FimH-competitive binding assays as well as

  FimH 是一种识别甘露糖的凝集素，通过引导其粘附和感染细胞的能力来表达。它涉及尿路感染和慢性病的发病机制。多项 X 射线结构引导配体设计研究被广泛用于小分子芳基甘露糖苷 FimH 拮抗剂的发现和优化。这些拮抗剂保留了甘露糖支架与 FimH 碳水化合物识别结构域的关键特异性相互作用。硫甘露糖苷是有吸引力且稳定的支架，这项工作报告了一些新的芳基和杂芳基衍生物作为 FimH 拮抗剂的合成。 FimH 竞争性结合测定以及新化合物的生物膜抑制（– 与参考 -庚基 α--吡喃甘露糖苷 () 进行比较而确定。发现这些化合物之间的亲和力受芳基和杂芳基的结构控制两种化合物的活性高于 分子对接和总疏水性与拓扑极性表面积的比值计算，这有助于解释所获得的生物学结果。本文描述的有效且合成上可行的FimH拮抗剂具有作为开发用于检测和治疗其疾病的传感器的先导的潜力。
• α-d-Mannose derivatives as models designed for selective inhibition of Golgi α-mannosidase II
  作者：Monika Poláková、Sergej Šesták、Erika Lattová、Ladislav Petruš、Ján Mucha、Igor Tvaroška、Juraj Kóňa

  DOI：10.1016/j.ejmech.2011.01.012

  日期：2011.3

  Human Golgi alpha-mannosidase II (hGM) is a pharmaceutical target for the design of inhibitors with antitumor activity. Nanomolar inhibitors of hGM exhibit unwanted co-inhibition of the human lysosomal alpha-mannosidase (hLM). Hence, improving specificity of the inhibitors directed toward hGM is desired in order to use them in cancer chemotherapy. We report on the rapid synthesis of D-mannose derivatives having one of the RS-. R(SO)- or R(SO(2))- groups at the alpha-anomeric position. Inhibitory properties of thirteen synthesized alpha-D-mannopyranosides were tested against the recombinant enzyme Drosophila melanogaster homolog of hGM (dGMIIb) and hLM (dLM408). Derivatives with the sulfonyl [R(SO(2))-] group exhibited inhibitory activities at the mM level toward both dGMIIb (IC(50) = 1.5-2.5 mM) and dLM408 (IC(50) = 1.0-2.0 mM). Among synthesized, only the benzylsulfonyl derivative showed selectivity toward dGMIIb. Its inhibitory activity was explained based on structural analysis of the built 3-D complexes of the enzyme with the docked compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.