【结 构 式】 |
【分子编号】35364 【品名】 【CA登记号】 |
【 分 子 式 】C57H88N4O14 【 分 子 量 】1053.34428 【元素组成】C 65% H 8.42% N 5.32% O 21.26% |
合成路线1
该中间体在本合成路线中的序号:(VIII)The acetylation of clarithromycin (I) with acetic anhydride gives the diacetate (II), which is acylated with CDI yielding the 12-O-(imidazolylcarbonyl) compound (III). The cyclization of (III) with ethylenediamine (IV) affords the cyclic carbamate (V), which is alkylated by reductocondensation with quinoline-3-carbaldehyde (VI) and NaBH(OAc)3 to give the secondary amine (VII). The methylation of this amine with formaldehyde and NaBH(OAc)3 yields the corresponding tertiary amine (VIII), which is treated with aqueous HCl to provide the descladinosyl compound (IX). Finally, this compound is acylated with 2-(2-pyridyl)acetic acid (X) by means of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (WSC) and deacetylated with methanol to afford the target compound.
【1】 Tanikawa, T.; Akashi, T.; Manaka, A.; Suzuki, K.; Asaka, T.; Adachi, T.; Ishii, T.; Sugiyama, H.; Kashimura, M.; Saito, H.; Morimoto, S.; Structure activity studies leading potent acyclides: 3-O-Acyl-5-O-desosaminylerythronolide 11,12-carbamates. 39th Intersci Conf Antimicrob Agents Chemother (Sept 26 1999, San Francisco) 1999, Abst F2159. |
【2】 Ishii, T.; Tanikawa, T.; Matsuura, A.; Sugimoto, T.; Asaka, T.; Kashimura, M. (Taisho Pharmaceutical Co., Ltd.); Erythromycin A derivs.. EP 0945459; WO 9823628 . |
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) | 35358 | C39H71NO12 | 详情 | 详情 | ||
(II) | 35359 | C43H75NO14 | 详情 | 详情 | ||
(III) | 35360 | C47H75N3O14 | 详情 | 详情 | ||
(IV) | 14754 | ethylenediamine;1,2-Diaminoethane;ethane-1,2-diamine;1,2-Ethanediamine | 107-15-3 | C2H8N2 | 详情 | 详情 |
(V) | 35361 | C46H79N3O14 | 详情 | 详情 | ||
(VI) | 35362 | 3-quinolinecarbaldehyde | 13669-42-6 | C10H7NO | 详情 | 详情 |
(VII) | 35363 | C56H86N4O14 | 详情 | 详情 | ||
(VIII) | 35364 | C57H88N4O14 | 详情 | 详情 | ||
(IX) | 35365 | (1R,2R,4R,6S)-2-[((3aS,4R,7R,8S,9S,10R,11R,13R,15R,15aR)-4-ethyl-8-hydroxy-11-methoxy-3a,7,9,11,13,15-hexamethyl-1-[2-[methyl(3-quinolinylmethyl)amino]ethyl]-2,6,14-trioxotetradecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazol-10-yl)oxy]-6-(dimethyl | C47H72N4O10 | 详情 | 详情 | |
(X) | 35366 | 2-(2-pyridinyl)acetic acid | 16179-97-8 | C7H7NO2 | 详情 | 详情 |