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【结 构 式】

【分子编号】62923

【品名】ethyl 2-{[(3aS,5S,6S,6aR)-6-hydroxy-5-(hydroxymethyl)-2-iminotetrahydrofuro[2,3-d][1,3]oxazol-3(2H)-yl]methyl}acrylate

【CA登记号】

【 分 子 式 】C12H18N2O6

【 分 子 量 】286.2848

【元素组成】C 50.35% H 6.34% N 9.79% O 33.53%

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:(XLIII)

Condensation of the bicyclic oxazoline (XV) with 2-(chloromethyl)acrylic acid ethyl ester (XLI) - obtained by treatment of the hydroxymethyl analogue (XLII) with SOCl2 - in dimethylacetamide gives the aduct (XLIII), which is treated first with hydroquinone and Na2CO3 in water and then with H2 over Pd/Al2O3 in the same solvent to provide 2,2'-anhydro-b-L-thymidine (XLIV). Reaction of compound (XLIV) with acetyl bromide in DMF/AcOEt yields 2'-bromo-3',5'-di-O-acetyl-b-L-thymidine (XLV), which is debrominated with H2 over Pd/Al2O3.to afford the 2'-deoxynucleoside (XLVI). Finally, this compound is deacetylated by means of NH3 in MeOH.

1 Sorbera, L.A.; Castañer, J.; Castañer, R.M.; Bayes, M.; Telbivudine. Drugs Fut 2003, 28, 9, 870.
2 Suzuki, T.; Iizuka, H.; Togashi, K. (Mitsui Chemicals, Inc.); L-Nucleic acid derivs. and processes for the synthesis thereof. EP 1348712; JP 2002241390; WO 0244194 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XV) 56918 (3aS,5S,6S,6aR)-5-(hydroxymethyl)-2-iminohexahydrofuro[2,3-d][1,3]oxazol-6-ol C6H10N2O4 详情 详情
(XLI) 62924 ethyl 2-(chloromethyl)acrylate C6H9ClO2 详情 详情
(XLII) 11327 ethyl 2-(hydroxymethyl)acrylate 10029-04-6 C6H10O3 详情 详情
(XLIII) 62923 ethyl 2-{[(3aS,5S,6S,6aR)-6-hydroxy-5-(hydroxymethyl)-2-iminotetrahydrofuro[2,3-d][1,3]oxazol-3(2H)-yl]methyl}acrylate C12H18N2O6 详情 详情
(XLIV) 62927 (2S,3S,3aR,9aS)-3-hydroxy-2-(hydroxymethyl)-7-methyl-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-6-one C10H12N2O5 详情 详情
(XLV) 12213 [(2R,3R,4R,5R)-3-(acetoxy)-4-bromo-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl acetate C14H17BrN2O7 详情 详情
(XLVI) 62928 {(2S,3R,5S)-3-(acetyloxy)-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl}methyl acetate C14H18N2O7 详情 详情
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