methyl 2-O-trifluoromethanesulfonyl-3-O-benzyl-(R)-4,6-O-benzylidene-α-D-glucopyranoside | 94160-77-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 2-O-trifluoromethanesulfonyl-3-O-benzyl-(R)-4,6-O-benzylidene-α-D-glucopyranoside
• 英文别名: methyl 3-O-benzyl-4,6-O-benzylidene-2-O-trifluoromethylsulfonyl-α-D-glucopyranoside；methyl 3-O-benzyl-4,6-O-benzylidene-2-O-trifluoromethanesulfonyl-α-D-glucopyranoside；[(2R,4aR,6S,7R,8S,8aR)-6-methoxy-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] trifluoromethanesulfonate
• CAS: 94160-77-7
• 化学式: C₂₂H₂₃F₃O₈S
• 分子量: 504.481
• InChiKey: GSOPZDIBBVOUEM-RZTRGMPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 2-O-trifluoromethanesulfonyl-3-O-benzyl-(R)-4,6-O-benzylidene-α-D-glucopyranoside 在 四丁基亚硝酸铵 作用下， 以 甲苯 为溶剂， 以70%的产率得到(2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
  参考文献：
  名称：

  Synthesis and binding affinity analysis of α1-2- and α1-6- O / S -linked dimannosides for the elucidation of sulfur in glycosidic bonds using quartz crystal microbalance sensors

  摘要：

  The role of sulfur in glycosidic bonds has been evaluated using quartz crystal microbalance methodology. Synthetic routes towards alpha 1-2- and alpha 1-6-linked dimannosides with S-or O-glycosidic bonds have been developed, and the recognition properties assessed in competition binding assays with the cognate lectin concanavalin A. Mannose-presenting QCM sensors were produced using photoinitiated, nitrenemediated immobilization methods, and the subsequent binding study was performed in an automated flow-through instrumentation, and correlated with data from isothermal titration calorimetry. The recorded Kd-values corresponded well with reported binding affinities for the O-linked dimannosides with affinities for the alpha 1-2-linked dimannosides in the lower micromolar range. The S-linked analogs showed slightly disparate effects, where the alpha 1-6-linked analog showed weaker affinity than the O-linked dimannoside, as well as positive apparent cooperativity, whereas the alpha 1-2-analog displayed very similar binding compared to the O-linked structure. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2017.09.015
• 作为产物：
  描述：

  3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 吡啶 、 盐酸 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 2-O-trifluoromethanesulfonyl-3-O-benzyl-(R)-4,6-O-benzylidene-α-D-glucopyranoside
  参考文献：
  名称：

  由D-甘露糖和D-葡萄糖合成1,5-二脱氧-1,5-亚氨基-D-甘露醇

  摘要：

  据报道（i）由D-甘露糖经5-叠氮基5-脱氧甘露糖的加氢反应，清楚地合成了1,5-二脱氧-1,5-亚氨基-D-甘露糖醇（LU1，1-deoxy-mannojirimycin）的对映体特异性。 （ii）来自D-葡萄糖，其中关键步骤涉及来自D-葡萄糖的C-2的三氟甲磺酰基的亲核取代。

  DOI：

  10.1016/0040-4039(84)80058-1

文献信息

• Non-Glycosidically Linked Pseudodisaccharides: Thioethers, Sulfoxides, Sulfones, Ethers, Selenoethers, and Their Binding to Lectins
  作者：Ian Cumpstey、Clinton Ramstadius、Tashfeen Akhtar、Irwin J. Goldstein、Harry C. Winter

  DOI：10.1002/ejoc.200901481

  日期：2010.4

  Hydrolytically stable non-glycosidically linked tail-to-tail pseudodisaccharides are linked by a single bridging atom remote from the anomeric centre of the constituent monosaccharides. Some such pseudodisaccharides with sulfur or oxygen bridges were found to act as disaccharide mimetics in their binding to the Banana Lectin and to Concanavalin A. A versatile synthetic route to a small library of such

  水解稳定的非糖苷连接的尾对尾假二糖通过远离组成单糖的异头中心的单个桥原子连接。发现一些具有硫桥或氧桥的此类假二糖在与香蕉凝集素和刀豆球蛋白 A 结合时充当二糖模拟物。描述了一种合成此类化合物的小型文库的通用途径。
• Mannosazide Methyl Uronate Donors. Glycosylating Properties and Use in the Construction of β-ManNAcA-Containing Oligosaccharides
  作者：Marthe T. C. Walvoort、Gerrit Lodder、Herman S. Overkleeft、Jeroen D. C. Codée、Gijsbert A. van der Marel

  DOI：10.1021/jo101779v

  日期：2010.12.3

  respectively. The β-S-phenyl mannosazide methyl uronate performed best in both activation experiments and glycosylation studies and provided the 1,2-cis mannosidic linkage with excellent selectivity. Consequently, an α-Glc-(1→4)-β-ManN3A-SPh disaccharide, constructed by the stereoselective glycosylation of a 6-O-Fmoc-protected glucoside and β-S-phenyl mannosazide methyl uronate, was used as the repetitive

  甘露糖苷尿酸甲酯供体具有多种异头离去基团（β-和α- S-苯基，β-和α- N-苯基三氟乙酰亚氨酸酯，羟基，β-亚砜以及（R s）-和（S s）-α -亚砜）置于活化条件下，并通过1 H NMR监测结果。虽然S-苯基和亚氨酸酯供体全部给出异头α-三氟甲磺酸的构象混合物，但半缩醛和β-和α-亚砜分别产生了三氟甲磺酸氧ulf和β-和α-bis双三氟甲磺酸。β一硫-苯基甘露糖苷尿酸甲酯在活化实验和糖基化研究中均表现最佳，并提供了1,2-顺式甘露糖苷键，具有出色的选择性。因此，α-Glc-（1→4）-β-MANN 3 A-SPh上二糖，由6-的立体选择性糖基化构建ö -Fmoc保护的葡糖苷和β-小号-苯基MAnnosazide甲基糖醛酸，被用来作为重复的供体结构单元，合成了对应于黄腐微球菌teurhuronic酸的三糖，五糖和七糖片段。
• Synthesis of a Trisaccharide and a Tetrasaccharide from the Cell-Wall Lipopolysaccharides of Azospirillum brasilense S17
  作者：Anup Misra、Shashi Pandey、Samir Ghosh

  DOI：10.1055/s-0029-1217401

  日期：2009.8

  A trisaccharide containing a d-mannosamine moiety and a tetrasaccharide containing an l-rhamnan chain that are found in the cell walls of Azospirillum brasilense S17 were synthesized concisely and in excellent yields. The key features of the synthetic strategy were stereoselective glycosylations and a minimum number of protecting-group manipulations. oligosaccharides - glycosylations - d-mannosamine

  简明地并且以优异的产率合成了在d.Asilspirillum brasilense S17的细胞壁中发现的包含d-甘露糖胺部分的三糖和包含1 - rhamnan链的四糖。合成策略的关键特征是立体选择性糖基化和最少数量的保护基操纵。 低聚糖-糖基化- d -mannosamine -巴西固氮螺菌-根瘤菌
• Facile synthesis of 4-deoxy-4-fluoro-α-d-talopyranoside, 4-deoxy-4-fluoro-α-d-idopyranoside and 2,4-dideoxy-2,4-difluoro-α-d-talopyranoside
  作者：Guy T. Giuffredi、Laura E. Jennings、Bruno Bernet、Véronique Gouverneur

  DOI：10.1016/j.jfluchem.2011.05.017

  日期：2011.10

  The title compounds were prepared by two independent syntheses using inexpensive commercially available starting materials. 4-Deoxy-4-fluoro-alpha--talopyranoside served as a precursor to 4-deoxy-4-fluoro-alpha-D-idopyranoside, allowing for inversion of configuration at C-3 via a three-step protocol. The synthesis of 2,4-dideoxy-2,4-difluoro-alpha-D-talopyranoside is based on two nucleophilic fluorination events at C-2 then at C-4 using TBAF center dot 3H(2)O and TBAF.4tBuOH as a fluoride source. All compounds are prepared as pure stereoisomers and are therefore suitable probes for OH center dot center dot center dot F H-bonding studies by (1)H NMR spectroscopy. (C) 2011 Elsevier B.V. All rights reserved.
• Efficient Two-Step Multifunctionalization of Substituted 2-Hydro­xyglycopyranosides
  作者：Antonio Franconetti、Francisca Cabrera-Escribano、Eleuterio Álvarez

  DOI：10.1055/s-0036-1588624

  日期：——

  A straightforward route to diversely functionalized glycopyranosides is reported. 2,3-Enopyranosides, 2- and/or 3-azido-, 2-halopyranosides, and a hex-3-ulose, among other - and -glycopyranosides are easily obtained in good to excellent yields from 2-hydroxyglycopyranosides by means of a two-step process involving trifluoromethanesulfonation and subsequent treatment with the appropriate nucleophilic agent.