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【结 构 式】

【分子编号】65918

【品名】 

【CA登记号】 

【 分 子 式 】C7H13FO4

【 分 子 量 】180.1762232

【元素组成】C 46.66% H 7.27% F 10.54% O 35.52%

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:(XV)

The methyl ribofuranose derivative (VIIIa) is prepared by addition of methyllithium to the furanone (XII) in ethyl ether to give the 2-C-methylarabinofuranose (XIII), which is converted to the 2-deoxy-2-fluoro-2-methylribofuranose derivative (XIV) by treatment with DAST in CH2Cl2. After debenzylation of compound (XIV) by transfer hydrogenolysis with Pd/C and cyclohexene, the deprotected compound (XV) is finally esterified with benzoyl chloride and pyridine (1-3). Scheme 2.

1 Clark, J. (Pharmasset Ltd.). Modified fluorinated nucleoside analogues. WO 2005003147.
2 Clark, J.L., Hollecker, L., Mason, J.C. Design, synthesis, and antiviral activity of 2’-deoxy-2’-fluoro-2’-C-methylcytidine, a potent inhibitor of hepatitis C virus replication. J Med Chem 2005, 48(17): 5504-8.
3 Clark, J. (Pharmasset, Inc.). Modified fluorinated nucleoside analogues. US 20080070861.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIIIA) 65911 ((2S,3S,4S)-3-(benzoyloxy)-4-fluoro-5-methoxy-4-methyltetrahydrofuran-2-yl)methyl benzoate   C21H21FO6 详情 详情
(XII) 65915 (4S,5S)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxydihydrofuran-3(2H)-one   C20H22O5 详情 详情
(XIII) 65916 (3S,4S,5S)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxy-3-methyltetrahydrofuran-3-ol   C21H26O5 详情 详情
(XIV) 65917 (3S,4S,5S)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-fluoro-2-methoxy-3-methyltetrahydrofuran   C21H25FO4 详情 详情
(XV) 65918     C7H13FO4 详情 详情
Extended Information