Methyl 2-O-benzyl-4,6-O-benzylidene-3-O-<(trifluoromethyl)sulfonyl>-β-D-glucopyranoside | 164322-53-6

• 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-benzyl-4,6-O-benzylidene-3-O-<(trifluoromethyl)sulfonyl>-β-D-glucopyranoside
• 英文别名: [(2R,4aR,6R,7R,8S,8aR)-6-methoxy-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] trifluoromethanesulfonate
• CAS: 164322-53-6
• 化学式: C₂₂H₂₃F₃O₈S
• 分子量: 504.481
• InChiKey: ISXGSRYCSGKVSF-JMPUJIDWSA-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-benzyl-4,6-O-benzylidene-3-O-<(trifluoromethyl)sulfonyl>-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 Methyl 2-O-benzyl-4,6-O-benzylidene-β-D-allopyranoside
  参考文献：
  名称：

  SN²Displacement of Carbohydrate Triflates by 9-Oximes of Erythromycin A and Of a Tylosin Derivative

  摘要：

  The preparation of 9-O-glycosyloxime derivatives of erythromycin A (1) and tylosin (2) is reported. Access to this new class of macrolides was achieved from (E)-9-oxime of erythromycin A (3) and 9-oxime of tylosin 20-(1,3-dithiane) (4), by successful displacement of triflates of suitably protected carbohydrates.

  DOI：

  10.1080/07328309608005695
• 作为产物：
  描述：

  三氟甲磺酸酐 、 methyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 Methyl 2-O-benzyl-4,6-O-benzylidene-3-O-<(trifluoromethyl)sulfonyl>-β-D-glucopyranoside
  参考文献：
  名称：

  非糖苷连接的假二糖：硫醚、亚砜、砜、醚、硒醚及其与凝集素的结合

  摘要：

  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。

  DOI：

  10.1002/ejoc.200901481

文献信息

• Ring Contraction vs Fragmentation in the Intramolecular Reactions of 3-O-(Trifluoromethanesulfonyl)pyranosides. Efficient Synthesis of Branched-Chain Furanosides
  作者：Mohamed Kassou、Sergio Castillon

  DOI：10.1021/jo00119a011

  日期：1995.7

  Intramolecular reactions of several methyl 3-O-triflylpyranosides of gluco, manno, galacto, and arabino (2-deoxy-gluco) configuration are studied. Triflates 1b-6b, of gluco, manno, and 8-deoxy-gluco configuration, give rise to ring-contraction products (branched-chain furanosides) 12, 15, 16, 17, 19, and 20, respectively. Triflates 7b and 10b of galacto configuration give the fragmentation products 21 and 23, whereas the 2-deoxy-galacto derivative 8b leads to ring-contraction product 20, which shows the decisive influence of the configuration at position 4 and the presence of a 2-alkoxy group on the reaction process. When the results from 4,6-O-benzylidene derivatives (1b-8b) and 4,6-di-O-benzyl derivatives (91b-11b) are compared, it turns out that the presence of a 4,6-O-benzylidene protecting group favors the formation of ring-contraction products. The use of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as the solvent and pyridine or 2,6-di-tert-butyl-4-methylpyridine as the base allowed us to obtain good to excellent yields of ring-contraction or fragmentation products.
• 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。
• SN²Displacement of Carbohydrate Triflates by 9-Oximes of Erythromycin A and Of a Tylosin Derivative
  作者：Cyrille Grandjean、Gabor Lukacs

  DOI：10.1080/07328309608005695

  日期：1996.9

  The preparation of 9-O-glycosyloxime derivatives of erythromycin A (1) and tylosin (2) is reported. Access to this new class of macrolides was achieved from (E)-9-oxime of erythromycin A (3) and 9-oxime of tylosin 20-(1,3-dithiane) (4), by successful displacement of triflates of suitably protected carbohydrates.