(2S,3R,4S,6R)-2-[[(3aS,4R,7R,8S,9S,10R,11R,13R,15R,15aR)-1-(4-chlorophenethyl)-4-ethyl-8-hydroxy-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,14-trioxotetradecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazol-10-yl]oxy]-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-3-yl acetate -Drug Synthesis Database

【结构式】

【分子编号】38158

【品名】(2S,3R,4S,6R)-2-[[(3aS,4R,7R,8S,9S,10R,11R,13R,15R,15aR)-1-(4-chlorophenethyl)-4-ethyl-8-hydroxy-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,14-trioxotetradecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazol-10-yl]oxy]-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-3-yl acetate

【CA登记号】

【分子式】C₄₁H₆₃ClN₂O₁₁

【分子量】795.4108

【元素组成】C 61.91% H 7.98% Cl 4.46% N 3.52% O 22.13%

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：(VI)

Protection of 2'-O-acetyl-6-O-methylerythromycin A (I) with chlorotrimethylsilane afforded the 4''-O-trimethylsilyl derivative (II). Subsequent treatment with carbonyldiimidazole and NaH produced the dehydrated imidazolide (III), which was converted to the cyclic carbamate (V) upon reaction with 4-chlorophenethyl amine (IV). Acid hydrolysis of the cladinose moiety gave alcohol (VI), and further condensation with carbonyldiimidazole yielded imidazolide (VII).

参考文献中间体

合成目标

【1】 Waid, P.; Dalton, C.R.; Randolph, J.T.; Greer, J.; Nichols, C.J.; Haviv, F.; Mort, N.A.; Sauer, D.R. (Abbott Laboratories Inc.); Macrolide LHRH antagonists. WO 0012522 .

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)	38154	(2S,3R,4S,6R)-4-(dimethylamino)-2-[((3R,4S,5R,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-12,13-dihydroxy-4-[[(4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxooxacyclotetradecanyl)oxy]-6-methyltetrahydro-2H-pyran-3-yl acetate		C₄₀H₇₁NO₁₄	详情	详情
(II)	38155	(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(3R,4S,5R,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-12,13-dihydroxy-7-methoxy-4-([(4R,5S,6S)-4-methoxy-4,6-dimethyl-5-[(trimethylsilyl)oxy]tetrahydro-2H-pyran-2-yl]oxy)-3,5,7,9,11,13-hexamethyl-2,10-dioxooxacyclotetradecanyl]oxy]-6-methyltetrahydro-2H-pyran-3-yl acetate		C₄₃H₇₉NO₁₄Si	详情	详情
(III)	38156	(2R,3S,7R,9R,10R,11R,12S,13R)-10-[[(2S,3R,4S,6R)-3-(acetoxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy]-2-ethyl-9-methoxy-12-([(4R,5S,6S)-4-methoxy-4,6-dimethyl-5-[(trimethylsilyl)oxy]tetrahydro-2H-pyran-2-yl]oxy)-3,5,7,9,11,13-hexamethyl-6,14-dioxooxa-4-cyclotetradecen-3-yl 1H-imidazole-1-carboxylate		C₄₇H₇₉N₃O₁₄Si	详情	详情
(IV)	29459	4-chlorophenethylamine; 2-(4-chlorophenyl)-1-ethanamine	156-41-2	C₈H₁₀ClN	详情	详情
(V)	38157	(2S,3R,4S,6R)-2-[[(3aS,4R,7R,8S,9R,10R,11R,13R,15R,15aR)-1-(4-chlorophenethyl)-4-ethyl-11-methoxy-8-([(4R,5S,6S)-4-methoxy-4,6-dimethyl-5-[(trimethylsilyl)oxy]tetrahydro-2H-pyran-2-yl]oxy)-3a,7,9,11,13,15-hexamethyl-2,6,14-trioxotetradecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazol-10-yl]oxy]-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-3-yl acetate		C₅₂H₈₅ClN₂O₁₄Si	详情	详情
(VI)	38158	(2S,3R,4S,6R)-2-[[(3aS,4R,7R,8S,9S,10R,11R,13R,15R,15aR)-1-(4-chlorophenethyl)-4-ethyl-8-hydroxy-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,14-trioxotetradecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazol-10-yl]oxy]-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-3-yl acetate		C₄₁H₆₃ClN₂O₁₁	详情	详情
(VII)	38159	(3aS,4R,7R,8S,9R,10R,11R,13R,15R,15aR)-10-[[(2S,3R,4S,6R)-3-(acetoxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy]-1-(4-chlorophenethyl)-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,14-trioxotetradecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazol-8-yl 1H-imidazole-1-carboxylate		C₄₅H₆₅ClN₄O₁₂	详情	详情

Extended Information