(2S,3S,4R,6R)-6-[((3R,4S,5R,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-3-(acetyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-12-{[(E)-5-(4-phenyl-1H-imidazol-1-yl)-2- -Drug Synthesis Database

【结构式】

【分子编号】62682

【品名】(2S,3S,4R,6R)-6-[((3R,4S,5R,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-3-(acetyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-12-{[(E)-5-(4-phenyl-1H-imidazol-1-yl)-2-

【CA登记号】

【分子式】C₅₆H₈₇N₃O₁₅

【分子量】1042.318

【元素组成】C 64.53% H 8.41% N 4.03% O 23.02%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(V)

Alkylation of clarithromycin diacetate (I) with allyl t-butyl carbonate (II) in the presence of palladium catalyst affords the 11-O-allyl ether (III). Subsequent metathesis reaction between ally ether (III) and 1-butenyl-4-phenylimidazole (IV) employing Grubb's catalyst provides adduct (V). Finally, methanolysis of the 2'-acetate ester of (V) gives rise to the target compound.

参考文献中间体

合成目标

【1】 Niu, D.; Phan, L.T.; Haley, T.; Polemeropoulos, A.; Or, Y.; Syntheses and antibacterial activities of novel 11-O-substituted macrolide and ketolide derivatives. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-1666.
【2】 Or, Y.S.; Phan, L.T.; Niu, D. (Enanta Pharmaceuticals, Inc.); 11-O-Substd. macrolides and their descladinose derivs.. US 2003114396; US 6673774; WO 0347600 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	53089	(2S,3S,4R,6R)-6-[((3R,4S,5R,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-3-(acetyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxooxacyclotetradecanyl)oxy]-4-methoxy-2,4-dimethyltetrahydro-2H-pyran-3-yl acetate	n/a	C₄₂H₇₃NO₁₅	详情	详情
(II)	62295	allyl tert-butyl carbonate		C₈H₁₄O₃	详情	详情
(III)	62680	(2S,3S,4R,6R)-6-{[(3R,4S,5R,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-3-(acetyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy}-12-(allyloxy)-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxooxacyclotetradecanyl]oxy}-4-		C₄₅H₇₇NO₁₅	详情	详情
(IV)	62681	1-(3-butenyl)-4-phenyl-1H-imidazole		C₁₃H₁₄N₂	详情	详情
(V)	62682	(2S,3S,4R,6R)-6-[((3R,4S,5R,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-3-(acetyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-12-{[(E)-5-(4-phenyl-1H-imidazol-1-yl)-2-		C₅₆H₈₇N₃O₁₅	详情	详情

Extended Information