methyl 2,3,6-tri-O-benzyl-4-O-(2,3,5-tri-O-benzoyl-α-D-lyxofuranosyl)-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-tri-O-benzyl-4-O-(2,3,5-tri-O-benzoyl-α-D-lyxofuranosyl)-α-D-glucopyranoside
• 英文别名: Bz(-2)[Bz(-3)][Bz(-5)]Lyxf(a1-4)[Bn(-2)][Bn(-3)][Bn(-6)]a-Glc1Me；[(2R,3S,4S,5R)-3,4-dibenzoyloxy-5-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxyoxolan-2-yl]methyl benzoate
• 化学式: C₅₄H₅₂O₁₃
• 分子量: 908.999
• InChiKey: AVQWMSODVQUIFU-ZKBKRGTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  67
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  METHYL-2,3,5-TRI-O-BENZOYL-A-D-*ARABINOFURANOSIDE 在 2,6-二甲基吡啶 、 gold(III) chloride 、 乙酰溴 、 四丁基碘化铵 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 methyl 2,3,6-tri-O-benzyl-4-O-(2,3,5-tri-O-benzoyl-α-D-lyxofuranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Gold(III)-Catalyzed Glycosidations for 1,2-trans and 1,2-cis Furanosides

  摘要：

  Stereoselective synthesis of furanosides is still a daunting task, unlike the pyranosides, for which several methods exist. Herein, a unified stereoselective strategy for the synthesis of 1,2-trans and 1,2-cis furanosides is revealed for seven out of eight possible isomers of pentoses. The identified protocol gives access to diastereoselective synthesis of α- and β-araf, ribf, lyxf, and α-xylf furanosides. 1,2-trans glycosides were synthesized by the use of propargyl 1,2-orthoesters under gold-catalyzed glycosidation conditions, and subsequently, they are converted into 1,2-cis glycosides through oxidation-reduction as the key functional group transformation. All the reactions are found to be fully diastereoselective, mild, and high yielding.

  DOI：

  10.1021/jo501052y