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Regioselective Synthesis of 1,3‐ and 1,2‐Tocopheryl Glyceride Ethers of Carboxylic Acids
Author(s) -
Choi Bo Seul,
Choi Jeongae,
Bak Seonyoung,
Koo Sangho
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403267
Subject(s) - chemistry , glyceride , regioselectivity , ether , organic chemistry , carboxylic acid , catalysis , fatty acid
Abstract A regioselective synthetic method with which to access 1,3‐tocopheryl glyceride ethers 2 of diverse carboxylic acids was developed through Bu 4 NBr‐catalyzed ring‐opening of tocopheryl glycidyl ether 1 . Steglich esterification of the 1,3‐tocopheryl acetyl‐glyceride ether 2a with various carboxylic acids, followed by selective deprotection of 3‐acetate by LiEt 3 BH reduction at –78 °C constitutes a regioselective synthetic method of 1,2‐tocopheryl glyceride ethers 4 . An example of the differing self‐assembled behavior of phosphorylcholine derivatives 6c and 7c of 1,3‐ and 1,2‐tocopheryl stearoyl‐glyceride ethers in aqueous solution is also described.