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【结 构 式】 
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【分子编号】33656 【品名】(3R,5R,6R,7R,9R,13S,14R)-6-([(2S,3R,4S,6R)-4-(dimethylamino)-6-methyl-3-[(trimethylsilyl)oxy]tetrahydro-2H-pyran-2-yl]oxy)-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11,13-hexamethyloxa-11-cyclotetradecene-2,4,10-trione 【CA登记号】 |
【 分 子 式 】C33H59NO9Si 【 分 子 量 】641.9183 【元素组成】C 61.75% H 9.26% N 2.18% O 22.43% Si 4.38% |
合成路线1
该中间体在本合成路线中的序号：(V)In an alternative synthesis, compound (IV) was protected as the silyl ether (V) and then fluorinated by means of N-fluorosulfonimide and potassium tert-butoxide. The resulting fluorinated derivative (VI) was desilylated by means of tetrabutylammonium fluoride to yield (VII), which was further protected as the 2'-acetate ester (VIII). Treatment of (VIII) with 1,1'-carbonyl diimidazole produced the acyl imidazole (IX). Subsequent condensation of (IX) with amine (X) gave rise to the corresponding 11,12-cyclic carbamate, which was finally deacetylated upon treatment with MeOH.
| 【1】 Bonnefoy, A.; Denis, A.; Novel fluoroketolides: Synthesis and antibacterial activity. Drugs Fut 2001, 26, 10, 975. |
| 【2】 Fromentin, C.; Denis, A.; Piltan, G.; Bretin, F.; Bonnet, A.; Agouridas, C.; Bonnefoy, A.; beta-Keto-ester chemistry and ketolides. Synthesis and antibacterial activity of 2-halogeno, 2-methyl and 2,3 enol-ether ketolides. Bioorg Med Chem Lett 2000, 10, 17, 2019. |
| 【3】 Spinnewyn, B.; Auguet, M.; Denis, A.; et al.; Synthesis and antibacterial activity of 2-halogeno, 2-methyl, and 2,3 enol-ether ketolides using beta-keto-ester chemistry. 39th Intersci Conf Antimicrob Agents Chemother (Sept 26 1999, San Francisco) 1999, Abst F2152. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 33655 | (3R,5R,6R,7R,9R,13S,14R)-6-[[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11,13-hexamethyloxa-11-cyclotetradecene-2,4,10-trione | C30H51NO9 | 详情 | 详情 | |
| (V) | 33656 | (3R,5R,6R,7R,9R,13S,14R)-6-([(2S,3R,4S,6R)-4-(dimethylamino)-6-methyl-3-[(trimethylsilyl)oxy]tetrahydro-2H-pyran-2-yl]oxy)-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11,13-hexamethyloxa-11-cyclotetradecene-2,4,10-trione | C33H59NO9Si | 详情 | 详情 | |
| (VI) | 33657 | (3S,5R,6R,7R,9R,13S,14R)-6-([(2S,3R,4S,6R)-4-(dimethylamino)-6-methyl-3-[(trimethylsilyl)oxy]tetrahydro-2H-pyran-2-yl]oxy)-14-ethyl-3-fluoro-13-hydroxy-7-methoxy-3,5,7,9,11,13-hexamethyloxa-11-cyclotetradecene-2,4,10-trione | C33H58FNO9Si | 详情 | 详情 | |
| (VII) | 33658 | (3S,5R,6R,7R,9R,13S,14R)-6-[[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-14-ethyl-3-fluoro-13-hydroxy-7-methoxy-3,5,7,9,11,13-hexamethyloxa-11-cyclotetradecene-2,4,10-trione | C30H50FNO9 | 详情 | 详情 | |
| (VIII) | 33659 | (2S,3R,4S,6R)-4-(dimethylamino)-2-[[(3S,5R,6R,7R,9R,13S,14R)-14-ethyl-3-fluoro-13-hydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,4,10-trioxooxa-11-cyclotetradecen-6-yl]oxy]-6-methyltetrahydro-2H-pyran-3-yl acetate | C32H52FNO10 | 详情 | 详情 | |
| (IX) | 33660 | (2R,3S,7R,9R,10R,11R,13S)-10-[[(2S,3R,4S,6R)-3-(acetoxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy]-2-ethyl-13-fluoro-9-methoxy-3,5,7,9,11,13-hexamethyl-6,12,14-trioxooxa-4-cyclotetradecen-3-yl 1H-imidazole-1-carboxylate | C36H54FN3O11 | 详情 | 详情 | |
| (X) | 17162 | 4-[4-(3-pyridinyl)-1H-imidazol-1-yl]butylamine; 4-[4-(3-pyridinyl)-1H-imidazol-1-yl]-1-butanamine | 173838-63-6 | C12H16N4 | 详情 | 详情 |