618-65-5Relevant articles and documents
Structure and reactivity of glycosides: IV. Koenigs-Knorr synthesis of aryl β-D-glucopyranosides using phase-transfer catalysts
Pavlov,Sokolov,Zakharov
, p. 1811 - 1814 (2007/10/03)
A series of acetylated aryl β-D-glucopyranosides were prepared in 12-63% yields from tetra-O-acetyl-α-D-glycopyranosyl bromide and phenols containing acyl, formyl, and hydroxy substituents, and also from sterically hindered phenols in the two-phase system chloroform-aqueous alkali in the presence of triethylbenzylammonium chloride. Hydroxyethylated sucrose and dibenzo-18-crown-6 do not behave as phase-transfer catalysts in glycosylation of phenols. 2001 MAIK "Nauka/Interperiodica".
PHASE-TRANSFER-CATALYZED D-GLUCOSYLATION:SYNTHESIS OF BENZOYLATED ARYL β-D-GLUCOPYRANOSIDES AND β-D-GLUCOPYRANOSYL-SUBSTITUTED CINNAMATES
Loganathan, Duraikkannu,Trivedi, Girish K.
, p. 117 - 126 (2007/10/02)
Phase-transfer-catalysed D-glucosylation of chelated phenolic aglucons and substituted cinnamic acids, using 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl bromide, resulted in the stereospecific formation of benzoylated aryl β-D-glucopyranosides and substituted-β-D-glucopyranosyl cinnamates, respectively, in good yields.The results conclusively disproved an earlier report that the phase-transfer method requires a nonparticipating group at C-2 or C-6 in the carbohydrate moiety. 1,2,3,4,6-Penta-O-benzoyl-β-D-glucopyranose was obtained as a minor side-product in all of these reactions.The possible mechanism of the phase-transfer method is discussed.