【结 构 式】 |
【分子编号】45917 【品名】(2S,3R,4S,6R)-4-(dimethylamino)-2-[((3R,5R,6R,7R,9R,12R,13R,14R)-13-hydroxy-7-methoxy-3,5,7,9,11,13,14-heptamethyl-12-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-2,4,10-trioxooxacyclotetradecanyl)oxy]-6-methyltetrahydro-2H-pyran-3-yl acetate 【CA登记号】 |
【 分 子 式 】C34H59NO11S 【 分 子 量 】689.9086 【元素组成】C 59.19% H 8.62% N 2.03% O 25.51% S 4.65% |
合成路线1
该中间体在本合成路线中的序号:(XI)Acidolysis of (VII) with HCl furnishes des(hexopyranosyloxy) derivative (VIII), which is then acetylated with acetic anhydride in ethyl acetate to give protected derivative (IX). Compound (IX) is then oxidized by treatment with 3-ethylcarbodiimide (EDCI) and pyridinium trifluoroacetate in DMSO/CH2Cl2 to afford ketone (X). Mesylation of (X) with methanesulfonyl chloride (MsCl) in pyridine yields mesylated derivative (XI), which is then converted into the 10,11-anhydro form (XII) by reaction with 1,8-Diazabicyclo(5.4.0)undec-7-ene (DBU) in acetone. Activation of compound (XII) by means of NaH and carbonyl diimidazole (CDI) in THF/DMF provides derivative (XIII), which is coupled with amine (XIV). Finally, treatment with refluxing MeOH furnishes the desired compound.
【1】 Chu, D.; Grant, E.; Hlasta, D.; Henninger, T.; Khosla, C. (Kosan Biosciences, Inc.; Ortho-McNeil Pharmaceutical, Inc.); Ketolide antibacterials. WO 0062783 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(XIIII) | 45919 | (2R,3S,7R,9R,10R,11R,13R)-10-[[(2S,3R,4S,6R)-3-(acetoxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy]-9-methoxy-2,3,5,7,9,11,13-heptamethyl-6,12,14-trioxooxa-4-cyclotetradecen-3-yl 1H-imidazole-1-carboxylate | C35H53N3O11 | 详情 | 详情 | |
(VII) | 45913 | (3R,4S,5R,6R,7R,9R,12R,13S,14R)-6-[[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-12,13-dihydroxy-4-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-7-methoxy-3,5,7,9,11,13,14-heptamethyl-2,10-oxacyclotetradecanedione | C37H67NO13 | 详情 | 详情 | |
(VIII) | 45914 | (3R,4S,5S,6R,7R,9R,12R,13S,14R)-6-[[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-4,12,13-trihydroxy-7-methoxy-3,5,7,9,11,13,14-heptamethyl-2,10-oxacyclotetradecanedione | C29H53NO10 | 详情 | 详情 | |
(IX) | 45915 | (2S,3R,4S,6R)-4-(dimethylamino)-6-methyl-2-[[(3R,4S,5S,6R,7R,9R,12R,13S,14R)-4,12,13-trihydroxy-7-methoxy-3,5,7,9,11,13,14-heptamethyl-2,10-dioxooxacyclotetradecanyl]oxy]tetrahydro-2H-pyran-3-yl acetate | C31H55NO11 | 详情 | 详情 | |
(X) | 45916 | (2S,3R,4S,6R)-2-[[(3R,5R,6R,7R,9R,12R,13S,14R)-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13,14-heptamethyl-2,4,10-trioxooxacyclotetradecanyl]oxy]-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-3-yl acetate | C31H53NO11 | 详情 | 详情 | |
(XI) | 45917 | (2S,3R,4S,6R)-4-(dimethylamino)-2-[((3R,5R,6R,7R,9R,12R,13R,14R)-13-hydroxy-7-methoxy-3,5,7,9,11,13,14-heptamethyl-12-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-2,4,10-trioxooxacyclotetradecanyl)oxy]-6-methyltetrahydro-2H-pyran-3-yl acetate | C34H59NO11S | 详情 | 详情 | |
(XII) | 45918 | (2S,3R,4S,6R)-4-(dimethylamino)-2-[[(3R,5R,6R,7R,9R,13S,14R)-13-hydroxy-7-methoxy-3,5,7,9,11,13,14-heptamethyl-2,4,10-trioxooxa-11-cyclotetradecen-6-yl]oxy]-6-methyltetrahydro-2H-pyran-3-yl acetate | C31H51NO10 | 详情 | 详情 | |
(XIV) | 45920 | 4-(4-quinolinyl)butylamine; 4-(4-quinolinyl)-1-butanamine | C13H16N2 | 详情 | 详情 |