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Original Articles

Glucosidation of Oleanolic and Ursolic Acidsunder Phase Transfer Catalysis

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Pages 47-50 | Received 12 May 1995, Published online: 04 Oct 2006

References

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  • Typical conditions: To a solution of the appropriate aglycone 1 or 2 (1,1 mmol) in aqueous 50% sodium hydroxide (12 ml) and benzyltributylammonium bromide (0.17 mmol) in 20 ml of dichloromethane, was added a solution of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 3a (8 mmol) in dichloromethane. The two phase reaction mixture was vigorously stirred at room temperature until TLC indicated that the reaction was complete (28 hours), CH2Cl2 was then added, the organic phase was separated and washed with 1,25 M sodium hydroxide and water. The combined organic extracts were dried (Na2SO4), filtred and evaporated in vacuo. The residueobtained was purified by flash chromatography (Silica gel, ethyl acetate/petroleum ether 3/2), afforded the corresponding saponins 1b (47%), 1c (22%) or 2b (50%), 2c (24%). Data given in tablel
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