- PHASE-TRANSFER-CATALYZED D-GLUCOSYLATION:SYNTHESIS OF BENZOYLATED ARYL β-D-GLUCOPYRANOSIDES AND β-D-GLUCOPYRANOSYL-SUBSTITUTED CINNAMATES
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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.
- Loganathan, Duraikkannu,Trivedi, Girish K.
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p. 117 - 126
(2007/10/02)
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