(2S,3R,4R,5S,6S)-5-(benzyloxy)-2-((2-(cyclopropylethynyl)benzoyl)oxy)-6-methyltetrahydro-2H-pyran-3,4-diyl dibenzoate | 1374991-26-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5S,6S)-5-(benzyloxy)-2-((2-(cyclopropylethynyl)benzoyl)oxy)-6-methyltetrahydro-2H-pyran-3,4-diyl dibenzoate
• CAS: 1374991-26-0
• 化学式: C₃₉H₃₄O₈
• 分子量: 630.694
• InChiKey: FYMPJFKWDMSKSH-GAJYMPBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.39
• 重原子数：
  47.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5,4'-di-O-acetyl-kaempferol 、 (2S,3R,4R,5S,6S)-5-(benzyloxy)-2-((2-(cyclopropylethynyl)benzoyl)oxy)-6-methyltetrahydro-2H-pyran-3,4-diyl dibenzoate 在 三苯基膦双(三氟甲磺酰亚胺)金 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到(2S,3R,4R,5S,6S)-2-((5-acetoxy-2-(4-acetoxyphenyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)oxy)-5-(benzyloxy)-6-methyltetrahydro-2H-pyran-3,4-diyl dibenzoate
  参考文献：
  名称：

  Efficient synthesis of kaempferol 3,7-O-bisglycosides via successive glycosylation with glycosyl ortho-alkynylbenzoates and trifluoroacetimidates

  摘要：

  Selective glycosylation of the 3-OH of 5,4'-di-O-acetyl-kaempferol was achieved with glycosyl orthoalkynylbenzoates as donors under the catalysis of Ph(3)PALINTf(2), and subsequent glycosylation of the remaining 7-OH with glycosyl trifluoroacetimidates under the catalysis of BF3.OEt2, after global deprotection, afforded the kaempferol 3,7-O-bisglycosides conveniently. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.03.103