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【结 构 式】 
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【分子编号】56703 【品名】[(2R,3R)-3-(benzoyloxy)-2,3-dihydro-2-furanyl]methyl benzoate 【CA登记号】 |
【 分 子 式 】C19H16O5 【 分 子 量 】324.33304 【元素组成】C 70.36% H 4.97% O 24.67% |
合成路线1
该中间体在本合成路线中的序号：(IV)The acylation of 2,3-O-isopropylidene-alpha-D-xylofuranose (I) with benzoyl chloride and pyridine gives the dibenzoyl ester (II), which is deprotected by means of H2SO4/HOAc in hot THF to yield 3,5-di-O-benzoyl-alpha-D-xylofuranose (III). The reaction of (III) with PPh3, I2 and imidazole in dichloromethane affords the glycal (IV), which is used in the glycosylation of the N,O-disilylated 5-fluorocytosine (V) by means of NIS in dichloromethane to provide the 2'-alpha-iodonucleoside (VI). The treatment of (VI) with Zn in EtOH/ethyl acetate (HOAc is used as catalyst) gives the unsaturated nucleoside (VII), which is finally debenzoylated by means of butylamine in THF.
| 【1】 Chen, S.-H.; Lin, S.; King, I.; Spinka, T.; Dutschman, G.E.; Gullen, E.A.; Cheng, Y.-C.; Doyle, T.W.; Synthesis and comparative evaluation of two antiviral agents: beta-L-Fd4C and beta-D-Fd4C. Bioorg Med Chem Lett 1998, 8, 22, 3245. |
| 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) | 41907 | (3aR,5R,6S,6aR)-5-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol | 20031-21-4 | C8H14O5 | 详情 | 详情 |
| (II) | 56701 | [(3aR,5R,6S,6aR)-6-(benzoyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate | C22H22O7 | 详情 | 详情 | |
| (III) | 56702 | [(2R,3R,4R,5S)-3-(benzoyloxy)-4,5-dihydroxytetrahydro-2-furanyl]methyl benzoate | C19H18O7 | 详情 | 详情 | |
| (IV) | 56703 | [(2R,3R)-3-(benzoyloxy)-2,3-dihydro-2-furanyl]methyl benzoate | C19H16O5 | 详情 | 详情 | |
| (V) | 36959 | 5-fluoro-N-(trimethylsilyl)-2-[(trimethylsilyl)oxy]-4-pyrimidinamine; N-[5-fluoro-2-[(trimethylsilyl)oxy]-4-pyrimidinyl]-N-(trimethylsilyl)amine | C10H20FN3OSi2 | 详情 | 详情 | |
| (VI) | 56704 | [(2R,3S,4R,5R)-5-[4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl]-3-(benzoyloxy)-4-iodotetrahydro-2-furanyl]methyl benzoate | C23H19FIN3O6 | 详情 | 详情 | |
| (VII) | 56705 | {(2S,5R)-5-[4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl]-2,5-dihydro-2-furanyl}methyl benzoate | C16H14FN3O4 | 详情 | 详情 |