(3R,4S,5R,6R)-3-(benzoyloxy)-4,5-bis(benzyloxy)-6-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-yl 2-(cyclopropylethynyl)benzoate | 1374991-23-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: (3R,4S,5R,6R)-3-(benzoyloxy)-4,5-bis(benzyloxy)-6-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-yl 2-(cyclopropylethynyl)benzoate
• CAS: 1374991-23-7
• 化学式: C₅₅H₅₄O₈Si
• 分子量: 871.114
• InChiKey: CYHCBNLOVAGIEC-MXDMNDRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  64.0
• 可旋转键数：
  15.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  89.52
• 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 、 (3R,4S,5R,6R)-3-(benzoyloxy)-4,5-bis(benzyloxy)-6-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-yl 2-(cyclopropylethynyl)benzoate 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70%的产率得到(3R,4S,5R,6R)-2-((5-acetoxy-2-(4-acetoxyphenyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)oxy)-4,5-bis(benzyloxy)-6-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydro-2H-pyran-3-yl benzoate
  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

文献信息

• Total Synthesis of Phellinus ribis Glycans with Immunostimulating Activities by an Orthogonal One-Pot Glycosylation Strategy
  作者：Jie Wan、Leilei Wang、Guozhi Xiao

  DOI：10.1055/a-1969-3992

  日期：2023.2

  achieved, which features orthogonal one-pot glycosylation strategy on the basis of N-phenyltrifluoroacetimidate (PTFAI) glycosylation, Yu glycosylation and ortho-(1-phenylvinyl)benzoate (PVB) glycosylation. The issues inherent to thioglycosides-based orthogonal one-pot glycosylation such as aglycone transfer have been precluded by this one-pot glycosylation strategy, which can streamline glycans chemical

  已经实现了具有强免疫刺激活性的桑黄聚糖的九糖重复单元和较短序列的全合成，其特点是基于 N-苯基三氟乙酰亚胺酯 (PTFAI) 糖基化、Yu 糖基化和邻位-(1-) 的正交一锅糖基化策略苯乙烯基）苯甲酸酯 (PVB) 糖基化。这种一锅糖基化策略排除了基于硫糖苷的正交一锅糖基化（如糖苷配基转移）所固有的问题，它可以简化聚糖的化学合成。