合成路线:The acylation of 3',4'-dideoxykanamycin B (dibekacin) (I) with N-benzyloxycarbonyloxysuccinimide (II) and zinc acetate in DMSO gives 3,2,6'-tri-N-benzyloxycarbonydibekacin (III),which is then treated with the N-hydroxysuccinimide ester of 2-hydroxy-4-aminobutyric acid (IV) and finally deprotected by hydrogenation with H2 over Pd/C in acidic water dioxane.
参考文献标题:Production of a selectively protected N-acylated derivative of an aminoglycosidic antibiotic
文献作者:Umezawa,H.; Umezawa,S.; Tsuchiya,T.; Takagi,Y.; Jikihara,T.(Microbial Chemistry Research Foundation)
参考来源:BE 0879925; DE 2945010; FR 2441631; FR 2482109; GB 2036020; GB 2065123; JP 80164696; JP 8064598; US 4297485
合成路线:The acylation of 3',4'-dideoxykanamycin B (dibekacin) (I) with tert-butyl-S-(4,6-dimethylpyrimid-2-yl)thiocarbonate (VIII) by means of triethylamine in isopropanol gives 3,2',6'-tri-N-tert-butyloxycarbonyldibekacin (IX),which is acylated again with 4-benzyloxycarbonylamino-2-hydroxybutyric acid N-hydroxysuccinimide ester (X) in THE yielding the protected habekacin (XI).Finally,this compound is deprotected by a treatment with trifluoroacetic acid,followed by hydrogenolysis with H2 over Pd/C in methanol - acetic acid.
参考文献标题:Process for the preparation of 1-N-isoseryl- or 1-N-(L-4-amino-2-hydroxybutyryl)-3',4'-dideoxykanamycin B and intermediates thereof
文献作者:Umezawa,H.; Kondo,S.(Microbial Chemistry Research Foundation)
参考来源:DE 2950020; FR 2444046; GB 2038329; GB 2072676; GB 2072677; JP 55081897; US 4268664
合成路线:The acylation of 3',4'-dideoxykanamycin B (dibekacin) (I) with N-benzyloxycarbonyloxysuccinimide (II) and zinc acetate in DMSO gives 3,2,6'-tri-N-benzyloxycarbonydibekacin (III),which is then treated with the N-hydroxysuccinimide ester of 2-hydroxy-4-aminobutyric acid (IV) and finally deprotected by hydrogenation with H2 over Pd/C in acidic water dioxane.
合成路线:The acylation of 3',4'-dideoxykanamycin B (dibekacin) (I) with benzyloxycarbonyl chloride in water gives 6'-N-benzyloxycarbonyldibekacin (V),which is then acylated with (IV) as before and deprotected by hydrogenolysis with H2 over Pd/C in water - acetic acid.
合成路线:The acylation of 3,2,6'-tri-N-benzyloxycarbonydibekacin (III) with ethyl trifluoroacetate and K2CO3 gives 3,2',6'-tri-N-benzyloxycarbonyl-3''-trifluoroacetyldibekacin (VI),which is acylated again with (IV) yielding the protected habekacin (VII).Finally,this compound is deprotected by hydrolysis with ammonia in aqueous THF,followed by hydrogenolysis with H2 over Pd/C.
合成路线:The acylation of 3',4'-dideoxykanamycin B (dibekacin) (I) with tert-butyl-S-(4,6-dimethylpyrimid-2-yl)thiocarbonate (VIII) by means of triethylamine in isopropanol gives 3,2',6'-tri-N-tert-butyloxycarbonyldibekacin (IX),which is acylated again with 4-benzyloxycarbonylamino-2-hydroxybutyric acid N-hydroxysuccinimide ester (X) in THE yielding the protected habekacin (XI).Finally,this compound is deprotected by a treatment with trifluoroacetic acid,followed by hydrogenolysis with H2 over Pd/C in methanol - acetic acid.
合成路线:The acylation of 3',4'-dideoxy-3',4'-didehydrokanamycin B (XII) with tert-butyl-S-(4,6-dimethylpyrimid-2-yl)thiocarbonate (VIII) as before gives 3,2',6'-tri-N-butoxycarbonyl-3',4'-dideoxy-3',4'-didehydrokanamycin B (XIII),which is acylated again with (X) as before yielding the fully protected 3',4'-didehydrohabekacin (XIV).Partial deprotection of (XIV) with trifluoroacetic acid affords 1-N-(4-benzyloxycarbonylamino-2-hydroxybutyryl)-3',4'-dideoxy-3',4'-didehydrokanamycin B (XV),which is finally debenzylated and reduced by a treatment with H2 over PtO2 in aqueous acetic acid.
参考文献标题:Habekacin
文献作者:Serradell,M.N.; Castar,J.; Blancafort,P.
参考来源:Drugs Fut 1983,8(5),410
合成路线:The acylation of 3,2,6'-tri-N-benzyloxycarbonydibekacin (III) with ethyl trifluoroacetate and K2CO3 gives 3,2',6'-tri-N-benzyloxycarbonyl-3''-trifluoroacetyldibekacin (VI),which is acylated again with (IV) yielding the protected habekacin (VII).Finally,this compound is deprotected by hydrolysis with ammonia in aqueous THF,followed by hydrogenolysis with H2 over Pd/C.
参考文献标题:1-N-Acylation of aminocyclitol antibiotics via zinc chelation and regiospecific N-trifluoroacetylation
文献作者:Tsuchiya,T.; Takagi,Y.; Umezawa,S.
参考来源:Tetrahedron Lett 1979,(51),4951-54
产品链接: CAS No. 51025-85-5››