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【结 构 式】 
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【分子编号】56694 【品名】(2S)-2-[(benzoyloxy)methyl]-1,3-dioxolan-4-yl 3-chlorobenzoate 【CA登记号】 |
【 分 子 式 】C18H15ClO6 【 分 子 量 】362.7662 【元素组成】C 59.6% H 4.17% Cl 9.77% O 26.46% |
合成路线1
该中间体在本合成路线中的序号：(IV)Displacement of the chlorine atom of (I) with potassium benzoate in boiling DMF afforded benzoate ester (II). The hydroxymethyl group of (II) was subsequently oxidized to carboxylic acid (III) employing pyridinium dichromate. Conversion of acid (III) to the corresponding mixed anhydride with ethyl chloroformate, followed by Baeyer-Villiger oxidation with m-chloroperbenzoic acid, gave rise to the m-chlorobenzoyloxy dioxolane (IV). This was then coupled to cytosine (V) following a previously reported procedure to produce adduct (VI) as a cis/trans mixture. After acetylation with Ac2O, the desired cis-isomer (VII) was isolated by flash chromatography. The title compound was finally obtained by basic hydrolysis (VII).
| 【1】 Belleau, B.; Dixit, D.; Nguyen-Ba, N. (Shire BioChem Inc.); 2-Substd.-4-substd.-1,3-dioxolanes, synthesis and use thereof. EP 0337713 . |
| 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) | 56692 | [(2S,4R)-2-(chloromethyl)-1,3-dioxolan-4-yl]methanol | C5H9ClO3 | 详情 | 详情 | |
| (II) | 56693 | [(2S,4R)-4-(hydroxymethyl)-1,3-dioxolan-2-yl]methyl benzoate | C12H14O5 | 详情 | 详情 | |
| (III) | 25844 | (2S,4S)-2-[(benzoyloxy)methyl]-1,3-dioxolane-4-carboxylic acid | C12H12O6 | 详情 | 详情 | |
| (IV) | 56694 | (2S)-2-[(benzoyloxy)methyl]-1,3-dioxolan-4-yl 3-chlorobenzoate | C18H15ClO6 | 详情 | 详情 | |
| (V) | 12706 | Cytosine; 4-Amino-2(1H)-pyrimidinone | 71-30-7 | C4H5N3O | 详情 | 详情 |
| (VI) | 56695 | {(2S)-4-[4-amino-2-oxo-1(2H)-pyrimidinyl]-1,3-dioxolan-2-yl}methyl benzoate | C15H15N3O5 | 详情 | 详情 | |
| (VII) | 56696 | {(2S,4S)-4-[4-(acetylamino)-2-oxo-1(2H)-pyrimidinyl]-1,3-dioxolan-2-yl}methyl benzoate | C17H17N3O6 | 详情 | 详情 |