药物详细合成路线

Name	Netilmicin sulfate;Sch-20569;Certomycin;Zetamicin;Netillin;Netromicine;Netromycin
Chemical Name	O-3-Deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1--6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1--4)]-2-deoxy-N1-ethyl-D-streptamine sulfate (2:5)
CAS	56391-57-2
Related CAS	56391-56-1 (free base)
Formula	C42H92N10O34S5
Structure
Formula Weight	1441.56814
Stage	上市-1981
Company	Schering-Plough (Originator), Essex (Not Determined), Menarini (Licensee)
Activity/Mechanism	Antibacterial Drugs, ANTIINFECTIVE THERAPY
Syn. Route	2

Route 1 by alkylation of sisomicin (i) with acetaldehyde (ii) and sodium cyanoborohydride in water with some sulfuric acid. List of intermediates No. n-[(3as,5s,6r,6ar)-5-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl]-n-(2-chloroethyl)urea (ii) [(2s,3s)-3-isopropyloxiranyl]methyl 2,2,2-trichloroethanimidoate (i) (1s)-2-methyl-1-[(4r)-2-(trichloromethyl)-4,5-dihydro-1,3-oxazol-4-yl]-1-propanol (iii) Reference 1:     castaner, j.; loren, j.g.; netilmicin. drugs fut 1978, 3, 7, 527. Reference 2:     wright, j.j.; synthesis of 1-n-ethylsisomicin: a broad-spectrum semisynthetic aminoglycoside antibiotic. j chem soc chem commun 1976, 6, 206-208. Reference 3:     daniels, p.j.l.; testa, r.; tattanahalli, l.; mallams, a.k.; wright, j.j.; weinstein, m.j.; wagman, g.h. (schering corp.); novel pseudotrisaccharides and methods for their production. de 2437160; fr 2240015; gb 1473733; us 4029882 . Route 2 the selective triacetylation of sisomicin (i) with zinc acetate, acetic anhydride and tea in methanol/thf gives the triacetate (ii), which is then alkylated with acetic acid and nabh4 in chloroform, affording 1-n-ethyl-3,2,6-tri-n-acetylsisomicin (iii). finally, this compound is deacetylated by means of refluxing aqueous naoh. List of intermediates No. [(2s,3s)-3-isopropyloxiranyl]methyl 2,2,2-trichloroethanimidoate (i) n-(8-amino-3,4-dimethyl-1-oxo-1,2-dihydro-7-isoquinolinyl)-n-(2,6-dichlorophenyl)thiourea (ii) 2,6-dichlorobenzenesulfonyl chloride (iii) Reference 1:     nam, g.; et al.; an efficient and selective 1-n-monoethylation of sisomicin: process development of netilmicin. org process res dev 2002, 6, 1, 78.

来源:药化网

作者:药化小编

摘要:本文合成路线介绍的是药物中文名硫酸奈替米星；英文名Netilmicin sulfate;Sch-20569;Certomycin;Zetamicin;Netillin;Netromicine;Netromycin；CAS[56391-57-2]

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