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.
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机译:5-(4-O-(4-ACYL-2,6-DIDEOXY-3-C-METHYL-DELTA-L-RIBOHEXOPYRANOSYLOSYL)-3,6-DIDEOXY-3-DIMETHYL-AMINO-BETA-的制备方法D-GluCOPYRANOSYLOXYLOXYL)-3-ACYLOXY-12,13-EPOXY-6-FORMYL-METHYL-9-HYDROXY-4-METHOXY-8-METHYL-10-HEXADECEN-15-Olide and 5-(4-O-(4-酰基-2,6-二去氧-3-C-甲基-δ-L-RIBOHEXOPYRA-NOSYL)-3,6-二去氧-3-二甲基氨基-BETA-D-葡糖基氨基Y基)-3-乙酰基-6-甲LM基-9, 13-二羟基-4-甲氧基-8-甲氧基-15-十六烷醇