2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→4)-1,6-anhydro-2,3-di-O-benzyl-β-D-glucopyranose | 1256394-00-9

• 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: 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→4)-1,6-anhydro-2,3-di-O-benzyl-β-D-glucopyranose
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[[(1R,2R,3S,4R,5R)-3,4-bis(phenylmethoxy)-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy]oxan-2-yl]methyl benzoate
• CAS: 1256394-00-9
• 化学式: C₅₄H₄₈O₁₄
• 分子量: 920.967
• InChiKey: WJKLCFZSIJYZFZ-WNSUEKNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  68
• 可旋转键数：
  21
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  161
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  在 gold(III) bromide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以68%的产率得到2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→4)-1,6-anhydro-2,3-di-O-benzyl-β-D-glucopyranose
  参考文献：
  名称：

  Gold-catalyzed glycosidations: synthesis of 1,6-anhydro saccharides

  摘要：

  Various 1,6-anhydro sugars are synthesized utilizing salient features of gold-catalyzed glycosidations. All the reactions occurred under mild conditions in the presence of 7 mol % of AuBr3 enabling easy synthesis of 1,6-anhydro sugars from corresponding 6-hydroxy propargyl/methyl monosaccharides, disaccharides, and trisaccharides in good yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.004

文献信息

• Thioperoxide-Mediated Activation of Thioglycoside Donors
  作者：Hongwen He、Xiangming Zhu

  DOI：10.1021/ol501211z

  日期：2014.6.6

  trimethylsilyl trifluoromethanesulfonate (TMSOTf) provides a powerful thiophilic promoter system, capable of activating different thioglycosides. Both armed and disarmed thioglycosides were activated effectively in the presence of different glycosyl acceptors, giving glycosidation products in high to excellent yields. A plausible activation pathway was also proposed and supported by isolating side-products

  硫过氧化物（1）与三甲基甲硅烷基三氟甲磺酸盐（TMSOTf）结合提供了强大的亲硫促进剂体系，能够活化不同的硫糖苷。在存在不同的糖基受体的情况下，武装和解除武装的硫代糖苷都被有效地激活，从而以高到极好的收率得到糖苷化产物。还提出了一条可行的活化途径，并通过分离副产物三氟甲基苯基二硫化物（CF 3 SSPh）和烯烃（42）予以支持。
• Gold-catalyzed glycosidations: synthesis of 1,6-anhydro saccharides
  作者：Shivaji A. Thadke、Srinivas Hotha

  DOI：10.1016/j.tetlet.2010.09.004

  日期：2010.11

  Various 1,6-anhydro sugars are synthesized utilizing salient features of gold-catalyzed glycosidations. All the reactions occurred under mild conditions in the presence of 7 mol % of AuBr3 enabling easy synthesis of 1,6-anhydro sugars from corresponding 6-hydroxy propargyl/methyl monosaccharides, disaccharides, and trisaccharides in good yields. (C) 2010 Elsevier Ltd. All rights reserved.