Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-iodo-phenoxy)-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester | 28713-06-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-iodo-phenoxy)-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
• CAS: 28713-06-6
• 化学式: C₃₂H₃₉IO₁₈
• 分子量: 838.555
• InChiKey: HRFILXMRGXIFGD-MMXCIQNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  51.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  221.02
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为产物：
  描述：

  4-碘苯酚 、 β-cellobioseoctaacetate 在 iron(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以70%的产率得到Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-iodo-phenoxy)-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  FeCl3-promoted and ultrasound-assisted synthesis of resveratrol O-derived glycoside analogs

  摘要：

  Phenol derived O-glycosides were synthesized using a direct and convenient O-glycosidation, starting from acetylated sugars in the presence of FeCl3, an inexpensive, mild and benign Lewis acid catalyst. The reactions were carried out under both conventional and ultrasonic irradiation conditions. In general, improvement in rates and yields were observed when reactions were carried out under sonication compared with conventional conditions leading to the corresponding beta-O-glycosides as the major anomer. Post-synthetic transformations of iodophenol intermediates led to new resveratrol O-glycoside analogs in good overall yields. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2014.05.022