2-methyl-3-buten-2-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside | 1300738-06-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-3-buten-2-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
• CAS: 1300738-06-0
• 化学式: C₁₉H₂₈O₁₀
• 分子量: 416.425
• InChiKey: JJNVWOBIVSJYKV-ICUGJSFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  2-甲基-3-丁烯-2-醇 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 silver trifluoromethanesulfonate 、 silver carbonate 作用下， 以 二氯甲烷 为溶剂， 以26%的产率得到2-methyl-3-buten-2-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  Semisynthesis of fuscoside B analogues and eunicosides, and analysis of anti-inflammatory activity

  摘要：

  A small library of semisynthetic analogues of fuscol and eunicol have been prepared and evaluated for in vivo topical anti-inflammatory activity using the mouse-ear edema assay. The first glycosylation of fuscol and eunicol has been achieved using a modified Koenigs-Knorr glycosylation to synthesize new fuscosides and eunicosides, a novel structural class of diterpene glycosides. The availability of adequate glycosylation methods for this synthesis was limited owing to the instability of the glycosyl acceptors. Glycosyl donor protecting group type had a pronounced effect on overall glycosylation yields of a model glycosyl acceptor. This synthesis provided access to the unnatural beta-glycosides allowing for an evaluation of the effect of differing anomeric stereochemistry on anti-inflammatory activity. The PEGylated derivatives of fuscol and eunicol were also synthesized by a convenient acid-promoted solvolysis of the natural product aglycones. This work highlights the importance of the glycan portion of fuscoside B. notably the stereochemical configuration of the glycosidic linkage, in the observed anti-inflammatory activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.006