(2S,3R,4S,6R)-4-(dimethylamino)-2-[((3R,5R,6R,7S,9R,11R,12R,13S,14R)-14-ethyl-12,13-dihydroxy-3,5,7,9,11,13-hexamethyl-2,4,10-trioxo-7-[[(E)-3-(3-quinolinyl)-2-propenyl]oxy]oxacyclotetradecanyl)oxy]-6-methyltetrahydro-2H-pyran-3-yl benzoate -Drug Synthesis Database

【结构式】

【分子编号】28433

【品名】(2S,3R,4S,6R)-4-(dimethylamino)-2-[((3R,5R,6R,7S,9R,11R,12R,13S,14R)-14-ethyl-12,13-dihydroxy-3,5,7,9,11,13-hexamethyl-2,4,10-trioxo-7-[[(E)-3-(3-quinolinyl)-2-propenyl]oxy]oxacyclotetradecanyl)oxy]-6-methyltetrahydro-2H-pyran-3-yl benzoate

【CA登记号】

【分子式】C₄₈H₆₄N₂O₁₁

【分子量】845.04304

【元素组成】C 68.22% H 7.63% N 3.32% O 20.83%

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：(IX)

Oxidation of the 3-hydroxyl group of (VI) by means of N-chlorosuccinimide in the presence of Me2S and Et3N produced ketone (VII). A 3-quinolinyl moiety was further introduced on the allyl group of (VII) by treatment with 3-bromoquinoline (VIII) in the presence of Pd(OAc)2 and tri-o-tolyl phosphine to yield (IX). Finally, the benzoate ester of (IX) was cleaved by treatment with boiling MeOH.

参考文献中间体

合成目标

【1】 Flamm, R.K.; Raney, P.M.; Nilius, A.M.; Bui, M.; Or, Y.S.; Wang, S.; Plattner, J.J.; Ma, Z.; Clark, R.; Chu, D.T.W.; Synthesis and antibacterial activity of 6-O-substituted ketolides. 38th Intersci Conf Antimicrob Agents Chemother (Sept 24 1998, San Diego) 1998, Abst F-126.
【2】 Or, Y.S.; Ma, Z.; Clark, R.F.; Chu, D.T.; Plattner, J.J. (Abbott Laboratories Inc.); 6-O-Substd. ketolides having antibacterial activity. EP 0929563; US 5866549; WO 9809978 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VI)	28430	(2S,3R,4S,6R)-2-[[(3R,4S,5S,6R,7S,9R,11R,12R,13S,14R)-7-(allyloxy)-14-ethyl-4,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-2,10-dioxooxacyclotetradecanyl]oxy]-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-3-yl benzoate		C₃₉H₆₁NO₁₁	详情	详情
(VII)	28431	(2S,3R,4S,6R)-2-[[(3R,5R,6R,7S,9R,11R,12R,13S,14R)-7-(allyloxy)-14-ethyl-12,13-dihydroxy-3,5,7,9,11,13-hexamethyl-2,4,10-trioxooxacyclotetradecanyl]oxy]-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-3-yl benzoate		C₃₉H₅₉NO₁₁	详情	详情
(VIII)	28432	3-bromoquinoline	5332-24-1	C₉H₆BrN	详情	详情
(IX)	28433	(2S,3R,4S,6R)-4-(dimethylamino)-2-[((3R,5R,6R,7S,9R,11R,12R,13S,14R)-14-ethyl-12,13-dihydroxy-3,5,7,9,11,13-hexamethyl-2,4,10-trioxo-7-[[(E)-3-(3-quinolinyl)-2-propenyl]oxy]oxacyclotetradecanyl)oxy]-6-methyltetrahydro-2H-pyran-3-yl benzoate		C₄₈H₆₄N₂O₁₁	详情	详情

Extended Information