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【结 构 式】 
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【分子编号】60187 【品名】1-{5-fluoro-3,4-bis[(phenylmethyl)oxy]tetrahydro-2-furanyl}ethyl phenylmethyl ether; 2-fluoro-3,4-bis[(phenylmethyl)oxy]-5-{1-[(phenylmethyl)oxy]ethyl}tetrahydrofuran 【CA登记号】 |
【 分 子 式 】C27H29FO4 【 分 子 量 】436.5232632 【元素组成】C 74.29% H 6.7% F 4.35% O 14.66% |
合成路线1
该中间体在本合成路线中的序号：(IV)Coupling of N-Boc-D-serine (I) with L-glutamic acid 1-methylamide 5-benzyl ester (II) by means of EDC and HOBt affords the dipeptide derivative (III). Subsequent glycosylation of the serine hydroxyl group of (III) with the perbenzylfucose donor (IV) in the presence of SnCl2 and AgOTf gives the alpha-glycoside (V). The N-Boc protecting group of (V) is removed under acidic conditions to furnish amine (VI), which is acylated by 2-tetradecylhexadecanoic acid (VII), yielding amide (VIII). The O-benzyl protecting groups of (VIII) are then removed by hydrogenolysis in the presence of Pearlman's catalyst, and the resultant carboxylic acid is finally converted to the corresponding arginine salt.
| 【1】 Hiramatsu, Y.; Moriyama, H.; Koyoi, T.; Tsukida, T.; Inoue, Y.; Kondo, H.; Studies on selectin blockers. 6. Discovery of homologous fucose sugar unit necessary for E-selectin binding. J Med Chem 1998, 41, 13, 2302. |
| 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) | 20126 | (2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropionic acid | C8H15NO5 | 详情 | 详情 | |
| (II) | 18551 | benzyl (4S)-4-amino-5-(methylamino)-5-oxopentanoate | C13H18N2O3 | 详情 | 详情 | |
| (III) | 60186 | phenylmethyl 4-{[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-hydroxypropanoyl]amino}-5-(methylamino)-5-oxopentanoate | C21H31N3O7 | 详情 | 详情 | |
| (IV) | 60187 | 1-{5-fluoro-3,4-bis[(phenylmethyl)oxy]tetrahydro-2-furanyl}ethyl phenylmethyl ether; 2-fluoro-3,4-bis[(phenylmethyl)oxy]-5-{1-[(phenylmethyl)oxy]ethyl}tetrahydrofuran | C27H29FO4 | 详情 | 详情 | |
| (V) | 60188 | phenylmethyl 4-{[3-[(3,4-bis[(phenylmethyl)oxy]-5-{1-[(phenylmethyl)oxy]ethyl}tetrahydro-2-furanyl)oxy]-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)propanoyl]amino}-5-(methylamino)-5-oxopentanoate | C48H59N3O11 | 详情 | 详情 | |
| (VI) | 60189 | phenylmethyl 4-({2-amino-3-[(3,4-bis[(phenylmethyl)oxy]-5-{1-[(phenylmethyl)oxy]ethyl}tetrahydro-2-furanyl)oxy]propanoyl}amino)-5-(methylamino)-5-oxopentanoate | C43H51N3O9 | 详情 | 详情 | |
| (VII) | 33399 | 2-methylpropionic acid | 79-31-2 | C4H8O2 | 详情 | 详情 |
| (VIII) | 60190 | phenylmethyl 4-({3-[(3,4-bis[(phenylmethyl)oxy]-5-{1-[(phenylmethyl)oxy]ethyl}tetrahydro-2-furanyl)oxy]-2-[(2-tetradecylhexadecanoyl)amino]propanoyl}amino)-5-(methylamino)-5-oxopentanoate | C73H109N3O10 | 详情 | 详情 |