2,7-dimethylocta-3,5-diyne-2,7-diyl bis(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside) | 1400767-46-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2,7-dimethylocta-3,5-diyne-2,7-diyl bis(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside)
• 英文别名: [(2R,3S,6R)-3-acetyloxy-6-[7-[[(2R,3S,6R)-3-acetyloxy-2-(acetyloxymethyl)-3,6-dihydro-2H-pyran-6-yl]oxy]-2,7-dimethylocta-3,5-diyn-2-yl]oxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1400767-46-5
• 化学式: C₃₀H₃₈O₁₂
• 分子量: 590.625
• InChiKey: WAHONOZTFNYYJW-BQXGFVACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  42
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  2-propynyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 copper(l) iodide 、 nickel(II) chloride hexahydrate 、 四甲基乙二胺 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以76%的产率得到2,7-dimethylocta-3,5-diyne-2,7-diyl bis(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside)
  参考文献：
  名称：

  Stereoselective synthesis of pseudoglycosides catalyzed by TeCl4 under mild conditions

  摘要：

  Catalytic amounts of tellurium(IV) tetrachloride were used to promote the O-glycosylation of 3,4,6-tri-O-acetyl-D-glucal to give the corresponding 2,3-unsaturated-O-glycosides. With simple alcohols, the desired compounds were obtained in good yields and excellent anomeric selectivity in a short reaction time using only 2 mol % of the catalyst. The application of the method in the synthesis of a small set of glycopyranosides with rigid or flexible linkers gave the corresponding alpha anomers as products in good yields. Further applications of some of the synthesized compounds in allylation reaction of aldehydes gave the corresponding homoallylic alcohols in good yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.070