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Regio‐ and Stereo‐selective Synthesis of Peracetylated Carbohydrate Esters of Aromatic Fatty Acid Using p ‐Toluenesulfonic Acid as Catalyst
Author(s) -
Zhu Zhenyuan,
Li Shengfeng,
Liu Rongqiang,
Yuan Jing,
Wang Haibiao,
Zhang Yongmin,
Liu Yang
Publication year - 2010
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201090371
Subject(s) - chemistry , yield (engineering) , stearic acid , p toluenesulfonic acid , catalysis , anomer , organic chemistry , fatty acid , glycosyl , carbohydrate , materials science , metallurgy
This paper describes an efficient synthesis of carbohydrate fatty acid esters based on a highly stereo‐ and regio‐selective esterification. The suitably protected glycosyl was esterified with stearic acid to give mainly the β ‐anomer in good yield using p ‐toluenesulfonic acid as catalyst. The structures of these compounds were fully confirmed by 1 H, 13 C NMR, mass spectra and HRMS.