合成路线:Orcinol (I) was acetylated with Ac2O in pyridine to give diacetate (II),which was submitted to a Fries rearrangement in the presence of AlCl3 in chlorobenzene at 90 C to afford acetophenone (III).Subsequent condensation of (III) with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide (IV) was effected either in the presence of CdCO3 in boiling toluene or K2CO3 and tributyl benzylammonium chloride in CH2Cl2 at r.t.The resulting (glucopyranosyloxy)acetophenone (V) was condensed with 5-formylbenzofuran (VI) in the presence of KOH to give chalcone (VII).Hydrogenation of (VII) over Pt/C then yielded the (benzofuranyl)propiophenone (VIII).After protection of the 6'-hydroxyl group of (VIII) as the allyl ether (X) with allyl bromide (IX) and K2CO3,the primary alcohol of (X) was acylated with ClCOOMe to furnish carbonate ester (XI).Finally,the O-allyl group of (XI) was cleaved with palladium catalyst and ammonium formate.
合成路线:Orcinol (I) is acetylated with Ac2O in pyridine giving the diacetate (II),which is submitted to a Fries rearrangement with AlCl3 in hot chlorobenzene yielding acetophenone (III).Subsequent condensation of (III) with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide (IV) by means of CdCO3 in refluxing toluene (or K2CO3 and tributylbenzylammonium chloride in dichloromethane) affords the glycosylated acetophenone (V),which is condensed with benzofuran-5-carbaldehyde (VI) by means of KOH in ethanol affording deacetylated chalcone (VII).Finally,this compound is hydrogenated with H2 over Pt/C in ethanol.
参考文献标题:Na+-glucose contransporter (SGLT) inhibitors as antidiabetic agents.4.Synthesis and pharmacological properties of 4'-dehydroxyphlorizin derivatives substituted on the B ring
文献作者:Tsujihara,K.; Hongu,M.; Saito,K.; Kawanishi,H.; Kuriyama,K.; Matsumoto,M.; Oku,A.; Ueta,K.; Tsuda,M.; Saito,A.
参考来源:J Med Chem 1999,42(26),5311
合成路线:Orcinol (I) was acetylated with Ac2O in pyridine to give diacetate (II),which was submitted to a Fries rearrangement in the presence of AlCl3 in chlorobenzene at 90 C to afford acetophenone (III).Subsequent condensation of (III) with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide (IV) was effected either in the presence of CdCO3 in boiling toluene or K2CO3 and tributyl benzylammonium chloride in CH2Cl2 at r.t.The resulting (glucopyranosyloxy)acetophenone (V) was condensed with 5-formylbenzofuran (VI) in the presence of KOH to give chalcone (VII).Hydrogenation of (VII) over Pt/C then yielded the (benzofuranyl)propiophenone (VIII).After protection of the 6'-hydroxyl group of (VIII) as the allyl ether (X) with allyl bromide (IX) and K2CO3,the primary alcohol of (X) was acylated with ClCOOMe to furnish carbonate ester (XI).Finally,the O-allyl group of (XI) was cleaved with palladium catalyst and ammonium formate.
参考文献标题:T-1095
文献作者:Doggrell,S.A.; Castar,J.
参考来源:Drugs Fut 2001,26(8),750
产品链接: CAS No. 209746-59-8››