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CAS 887125-82-8

Acetic acid (2S,3R,4S,6R)-4-(dimethylamino)-2-[((3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-10-[[(1-isopropoxycyclohexyl)oxy]imino]-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yl)oxy]-6-methyltetrahydropyran-3-yl ester

Codes: Clarithromycin-007

Application context (from source-drug indications)

Marginal zone B-cell lymphomaClarithromycin/Rabeprazole Sodium/AmoxicillinDuodenal ulcerClarithromycin/Rabeprazole Sodium/AmoxicillinImmune thrombocytopenic purpuraClarithromycin/Rabeprazole Sodium/AmoxicillinGastric ulcerClarithromycin/Rabeprazole Sodium/AmoxicillinGastritisClarithromycin/Rabeprazole Sodium/AmoxicillinHelicobacter pylori infectionClarithromycin/Rabeprazole Sodium/AmoxicillinSinusitisClarithromycinTonsillitisClarithromycinAcute bronchitisClarithromycinChronic bronchitisClarithromycinLower respiratory tract infectionClarithromycinPharyngitisClarithromycin

Source drugs (routes using this intermediate)

DrugTierExpiry
Clarithromycin/Rabeprazole Sodium/AmoxicillinTier C — Watch / trade-
ClarithromycinTier C — Watch / trade-

Position in synthesis routes (up/downstream chain)

Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.

Clarithromycin/Rabeprazole Sodium/AmoxicillinOptimised routesteps: 4total yield: 18g(Clarithromycin (Free))
(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydropyran-2-yloxy]-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydrpyran-2-yloxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione 10-[O-(1-isopropoxycyclohexyl)oxime]→Acetic acid (2S,3R,4S,6R)-4-(dimethylamino)-2-[((3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-10-[[(1-isopropoxycyclohexyl)oxy]imino]-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yl)oxy]-6-methyltetrahydropyran-3-yl ester→Benzoic acid (2S,3R,4S,6R)-4-(dimethylamino)-2-[((3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-10-[[(1-isopropoxycyclohexyl)oxy]imino]-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yl)oxy]-6-methyltetrahydropyran-3-yl ester→Benzoic acid (2S,3R,4S,6R)-4-(dimethylamino)-2-[(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-10-[[(1-isopropoxycyclohexyl)oxy]imino]-7-methoxy-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yloxy]-6-methyltetrahydropyran-3-yl ester→Acetic acid (2S,3R,4S,6R)-4-(dimethylamino)-2-[((3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-10-[[(1-isopropoxycyclohexyl)oxy]imino]-7-methoxy-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yl)oxy]-6-methyltetrahydropyran-3-yl ester→(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydropyran-2-yloxy]-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione 10-[O-(1-isopropoxycyclohexyl)oxime]
ClarithromycinOptimised routesteps: 4total yield: 18g(Clarithromycin (Free))
(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydropyran-2-yloxy]-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydrpyran-2-yloxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione 10-[O-(1-isopropoxycyclohexyl)oxime]→Acetic acid (2S,3R,4S,6R)-4-(dimethylamino)-2-[((3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-10-[[(1-isopropoxycyclohexyl)oxy]imino]-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yl)oxy]-6-methyltetrahydropyran-3-yl ester→Benzoic acid (2S,3R,4S,6R)-4-(dimethylamino)-2-[((3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-10-[[(1-isopropoxycyclohexyl)oxy]imino]-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yl)oxy]-6-methyltetrahydropyran-3-yl ester→Benzoic acid (2S,3R,4S,6R)-4-(dimethylamino)-2-[(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-10-[[(1-isopropoxycyclohexyl)oxy]imino]-7-methoxy-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yloxy]-6-methyltetrahydropyran-3-yl ester→Acetic acid (2S,3R,4S,6R)-4-(dimethylamino)-2-[((3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-10-[[(1-isopropoxycyclohexyl)oxy]imino]-7-methoxy-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yl)oxy]-6-methyltetrahydropyran-3-yl ester→(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydropyran-2-yloxy]-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione 10-[O-(1-isopropoxycyclohexyl)oxime]

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