AIM:To simplify the procedure for synthesis of 2′ acetyl 12 hydroxy 2,3,10,11 dianhydro 6 O methyl erythromycin A(7). METHOD:Selective removal of the cladinose residue of clarithromycin was accomplished by the treatm...AIM:To simplify the procedure for synthesis of 2′ acetyl 12 hydroxy 2,3,10,11 dianhydro 6 O methyl erythromycin A(7). METHOD:Selective removal of the cladinose residue of clarithromycin was accomplished by the treatment with aqueous HCl at room temperature. Acetylation with acetic anhydride/triethylamine in methylene chloride provided the 2′ protected macrolide(9) with high yield. Then 2′ acetyl 12 hydroxy 2,3,10,11 dianhydro 6 O methyl erythromycin A(7) was synthesized from 9 which was treated with excess p toluenesulfonic acid and triethyl orthoformate at 50 ℃ in acetone.RESULT:The overall yield was 27%. The structure of the product was confirmed by IR,MS,NMR and elemental analysis. CONCLUSION: Our synthetic procedure of 7 was shorter and more convenient than that reported by Abbott Laboratories.展开更多
The synthesis of oestradiol compounds,which plays a very important role in biochemical test,is described in this paper.2-Hydroxide-17-deoxy-oestrone was synthesized from oestrone dy a three-step procedure:Wolff-Kishne...The synthesis of oestradiol compounds,which plays a very important role in biochemical test,is described in this paper.2-Hydroxide-17-deoxy-oestrone was synthesized from oestrone dy a three-step procedure:Wolff-Kishner reduction,acetylation and Dakin oxidation.(1) WolffKishner reduction: the yield of 17-deoxyestrone was 86.0%.(2)acetylation:the yield of 2-acetyl-deoxyestrone was 81.9%.(3) Dakin oxidation: the yield of 2hydroxied-17deoxy-oestrone was 91.2%展开更多
文摘AIM:To simplify the procedure for synthesis of 2′ acetyl 12 hydroxy 2,3,10,11 dianhydro 6 O methyl erythromycin A(7). METHOD:Selective removal of the cladinose residue of clarithromycin was accomplished by the treatment with aqueous HCl at room temperature. Acetylation with acetic anhydride/triethylamine in methylene chloride provided the 2′ protected macrolide(9) with high yield. Then 2′ acetyl 12 hydroxy 2,3,10,11 dianhydro 6 O methyl erythromycin A(7) was synthesized from 9 which was treated with excess p toluenesulfonic acid and triethyl orthoformate at 50 ℃ in acetone.RESULT:The overall yield was 27%. The structure of the product was confirmed by IR,MS,NMR and elemental analysis. CONCLUSION: Our synthetic procedure of 7 was shorter and more convenient than that reported by Abbott Laboratories.
基金supported by the National Natural Science Foundation of China(31271181,21263002)Natural Science Foundation of Jiangsu Province,China(BK2011811)Guangxi Natural Science Foundation,China(2013GXNSFAA019024)~~
文摘The synthesis of oestradiol compounds,which plays a very important role in biochemical test,is described in this paper.2-Hydroxide-17-deoxy-oestrone was synthesized from oestrone dy a three-step procedure:Wolff-Kishner reduction,acetylation and Dakin oxidation.(1) WolffKishner reduction: the yield of 17-deoxyestrone was 86.0%.(2)acetylation:the yield of 2-acetyl-deoxyestrone was 81.9%.(3) Dakin oxidation: the yield of 2hydroxied-17deoxy-oestrone was 91.2%
