O¹-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(R)-mandelamide | 488817-84-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: O¹-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(R)-mandelamide
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(1R)-2-amino-2-oxo-1-phenylethoxy]oxan-2-yl]methyl acetate
• CAS: 488817-84-1
• 化学式: C₂₂H₂₇NO₁₁
• 分子量: 481.456
• InChiKey: QXCHUKFHDDLXBX-DPAHKSBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  167
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  O¹-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(R)-mandelamide 在 吡啶 、 sodium methylate 、 三氟乙酸酐 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 O¹-β-D-galactopyranosylmandelonitrile
  参考文献：
  名称：

  SYNTHESIS OF CHLORAMPHENICOL AND MANDELONITRILE GALACTOSE-CONTAINING PRODRUGS

  摘要：

  The synthesis of O-1-beta-D-galactopyranosylchloramphenicol and O-1-beta-D-galactopyranosylmandelonitrile as prodrugs potentially substrates of beta-galactosidase, are reported. Preparation of O-1-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl) chloramphenicol from unprotected chloramphenicol was successful using beta-D-galactopyranose pentaacetate and boron trifluoride diethyl etherate in acetonitrile. However, the beta-galactosylated diastereoisomers of racemic mandelonitrile had to be made via O-1-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)mandelamide in dichloromethane prior to dehydration to obtain the nitrile moiety. Indeed, galactosylation trials starting directly from mandelonitrile in acetonitrile led to the O-1-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)mandelonitrile diastereoisomers. From a methodological point of view, this work extends the use of the galactosylation method to new hydroxyl bearing compounds. It also points out that the solvent used (acetonitrile or dichloromethane) and the purity of boron trifluoride diethyl etherate can be crucial factors in the use of this method as an eventual alternative to heavy metal-based Lewis acids usually employed in glycosylation reactions.

  DOI：

  10.1081/car-120013493
• 作为产物：
  描述：

  (±)-扁桃酰胺 、 beta-D-半乳糖五乙酸酯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以33%的产率得到O¹-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(R)-mandelamide
  参考文献：
  名称：

  SYNTHESIS OF CHLORAMPHENICOL AND MANDELONITRILE GALACTOSE-CONTAINING PRODRUGS

  摘要：

  The synthesis of O-1-beta-D-galactopyranosylchloramphenicol and O-1-beta-D-galactopyranosylmandelonitrile as prodrugs potentially substrates of beta-galactosidase, are reported. Preparation of O-1-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl) chloramphenicol from unprotected chloramphenicol was successful using beta-D-galactopyranose pentaacetate and boron trifluoride diethyl etherate in acetonitrile. However, the beta-galactosylated diastereoisomers of racemic mandelonitrile had to be made via O-1-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)mandelamide in dichloromethane prior to dehydration to obtain the nitrile moiety. Indeed, galactosylation trials starting directly from mandelonitrile in acetonitrile led to the O-1-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)mandelonitrile diastereoisomers. From a methodological point of view, this work extends the use of the galactosylation method to new hydroxyl bearing compounds. It also points out that the solvent used (acetonitrile or dichloromethane) and the purity of boron trifluoride diethyl etherate can be crucial factors in the use of this method as an eventual alternative to heavy metal-based Lewis acids usually employed in glycosylation reactions.

  DOI：

  10.1081/car-120013493