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【结 构 式】

【分子编号】61368

【品名】(2S,3S,4R,5R)-3-azido-5-(6-chloro-9H-purin-9-yl)-4-hydroxy-N-methyltetrahydro-2-furancarboxamide

【CA登记号】

【 分 子 式 】C11H11ClN8O3

【 分 子 量 】338.71316

【元素组成】C 39.01% H 3.27% Cl 10.47% N 33.08% O 14.17%

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:(X)

Treatment of 1,2,5,6-diisopropylidene-D-glucofuranose (I) with trifluoromethanesulfonic anhydride and pyridine provides triflate (II), which is then displaced with sodium azide to furnish the 3-azido derivative (III). Oxidative cleavage of the 5,6-diol acetonide of (III) by means of periodic acid leads to aldehyde (IV). Further oxidation of (IV) with a catalytic amount of ruthenium trichloride in the presence of sodium periodate affords carboxylic acid (V). After activation of acid (V) with oxalyl chloride, coupling with methylamine provides amide (VI). Acidic hydrolysis of the remaining 1,2-acetonide of (VI) in the presence of acetic anhydride gives rise to diacetate (VII). Silylation of 6-chloropurine (VIII), followed by coupling with the diacetyl ribofuranuronic acid derivative (VII) in the presence of trimethylsilyl triflate yields the purine glycoside (IX). The acetate ester group of (IX) is then removed by methanolysis in the presence of either methylamine or triethylamine, to produce alcohol (X). Subsequent azido group reduction in (X) by means of triphenylphosphine leads to amine (XI), which is then protected as the N-Boc derivative (XII) employing di-t-butyl dicarbonate.

1 Masamune, H.; Scott, R.W.; Deninno, M.P. (Pfizer Products Inc.); Cpds. for the treatment of ischemia. EP 1216257; JP 2003510331; WO 0123399 .
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) 29141 (3aR,5S,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol 582-52-5 C12H20O6 详情 详情
(II) 61299 (3aR,5R,6S,6aR)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl trifluoromethanesulfonate C13H19F3O8S 详情 详情
(III) 61300 (3aR,5S,6R,6aR)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl azide; (3aR,5S,6R,6aR)-6-azido-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole C12H19N3O5 详情 详情
(IV) 61363 (3aR,5S,6R,6aR)-6-azido-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde C8H11N3O4 详情 详情
(V) 31364 (5E)-2-[(Z,4E)-6-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-methyl-4-hexenylidene]-6,10-dimethyl-5,9-undecadienal C28H35NO3 详情 详情
(VI) 31365 tert-butyl[[(2E,6Z,10E)-7-(diethoxymethyl)-3,11,15-trimethyl-2,6,10,14-hexadecatetraenyl]oxy]dimethylsilane; tert-butyl(dimethyl)silyl (2E,6Z,10E)-7-(diethoxymethyl)-3,11,15-trimethyl-2,6,10,14-hexadecatetraenyl ether C30H56O3Si 详情 详情
(VII) 31366 2-[(2E,6Z,10E)-7-(hydroxymethyl)-3,11,15-trimethyl-2,6,10,14-hexadecatetraenyl]-1H-isoindole-1,3(2H)-dione C28H37NO3 详情 详情
(VIII) 17692 6-Chloropurine; 6-chloro-9H-purine 87-42-3 C5H3ClN4 详情 详情
(IX) 61367 (2R,3R,4R,5S)-4-azido-2-(6-chloro-9H-purin-9-yl)-5-[(methylamino)carbonyl]tetrahydro-3-furanyl acetate C13H13ClN8O4 详情 详情
(X) 61368 (2S,3S,4R,5R)-3-azido-5-(6-chloro-9H-purin-9-yl)-4-hydroxy-N-methyltetrahydro-2-furancarboxamide C11H11ClN8O3 详情 详情
(XI) 61369 (2S,3S,4R,5R)-3-amino-5-(6-chloro-9H-purin-9-yl)-4-hydroxy-N-methyltetrahydro-2-furancarboxamide C11H13ClN6O3 详情 详情
(XII) 61370 tert-butyl (2S,3S,4R,5R)-5-(6-chloro-9H-purin-9-yl)-4-hydroxy-2-[(methylamino)carbonyl]tetrahydro-3-furanylcarbamate C16H21ClN6O5 详情 详情
Extended Information