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【结 构 式】

【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%

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:(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
Extended Information