Premium
Preparation of some linseed esters of methyl a ‐ d ‐glucopyranoside using the methoxycarbonyl blocking group
Author(s) -
Dufek E. J.,
DeJarlais W. J.
Publication year - 1965
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02636921
Subject(s) - anhydrous , chemistry , glucoside , derivative (finance) , methyl group , blocking (statistics) , block (permutation group theory) , stereochemistry , group (periodic table) , organic chemistry , alternative medicine , medicine , statistics , mathematics , geometry , pathology , financial economics , economics
The three possible methoxycarbonyl derivatives of methyl 4,6‐ O ‐benzylidene‐ a ‐ d ‐glucopyranoside have been prepared. The methoxycarbonyl at the C 2 position in the 2,3‐di‐ O ‐methoxycarbonyl derivative is removed selectively in anhydrous ammonia. The ability of the methoxycarbonyl group to block selectively the C 2 hydroxyl in methyl glucoside has been utilized to synthesize some mono‐, di‐, and tri‐linseed esters of methyl glucoside. The use of this new blocking group has permitted the first synthesis of some unsaturated esters of methyl glucoside.