Novel synthesis of steryl esteryl esters from β-sitosterol and N-phosphoryl amino acid under microwave irradiation

GRAPHICAL ABSTRACT

ABSTRACT

Ten novel N-phosphoryl amino acids β-sitosterol esters were synthesized by coupling the N-phosphoryl amino acids with β-sitosterol under microwave irradiation, and their structures were elucidated by IR, NMR, and HR MS. Various reaction conditions including the catalyst, solvent, temperature and time were investigated. Under the optimal conditions, the reaction was finished in 20 min with 60–87% yields by employing DCC/DMAP as a catalyst system at room temperature.

KEYWORDS:

• β-Sitosterol
• N-phosphoryl amino acid
• esterification
• steryl ester
• microwave irradiation

Funding

We acknowledge financial support from the National Natural Science Foundation of China (No. 21302042 and 21172055), Department of Henan Province Natural Science and Technology Foundation (No. 142102210410), Natural Science Foundation in Henan Province Department of Education (No. 14B150053), the Program for Innovative Research Team from Zhengzhou (No. 131PCXTD605), and Natural Science Foundation from Technology Bureau of Zhengzhou (No. 20130883).