【结 构 式】 |
【分子编号】47155 【品名】 【CA登记号】 |
【 分 子 式 】C21H22O9 【 分 子 量 】418.40028 【元素组成】C 60.28% H 5.3% O 34.42% |
合成路线1
该中间体在本合成路线中的序号:(V)The reaction of the spiro compound (I) with CDI in refluxing dichloroethane gives the cyclic carbonate (II), which is condensed with the benzopyranone (III) by means of DEAD and PPH3 in DMF, yielding the adduct (IV). Elimination of the diphenylmethyl protecting group by hydrogenation with H2 over Pd/C in THF affords compound (V), which is acylated with acetic anhydride to provide the acetyl derivative (VI). The reaction of (VI) with O-(2-propynyl)hydroxylamine (VII) by means of LiClO4 gives the propargyloxycarbamate (VIII) as a mixture of regioisomers that are separated by chromatography. The opening of the carbonate ring of (VII) is accompanied by the formation of the corresponding oxime at the acetyl group of the benzopyran. This oxime is easily exchanged for methoxy by reaction with an excess of O-methoxyhydroxylamine and K-OAc in ethanol to give rise to the target compound.
【1】 Laurin, P.; Periers, A.-M.; Musicki, B.; et al.; Improved antibacterial activities of coumarin antibiotics bearing 5',5'-dialkylnoviose: Biological activity of RU79115. Bioorg Med Chem Lett 2000, 10, 15, 1695. |
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) | 38187 | (8R,9S,10R)-10-methoxy-6-oxaspiro[4.5]decane-7,8,9-triol | C10H18O5 | 详情 | 详情 | |
(II) | 47153 | C11H16O6 | 详情 | 详情 | ||
(III) | 38188 | 4-(benzhydryloxy)-7-hydroxy-8-methyl-2H-chromen-2-one | C23H18O4 | 详情 | 详情 | |
(IV) | 47154 | C34H32O9 | 详情 | 详情 | ||
(V) | 47155 | C21H22O9 | 详情 | 详情 | ||
(VI) | 47156 | C23H24O10 | 详情 | 详情 | ||
(VII) | 38197 | O-(2-propynyl)hydroxylamine; 3-(aminooxy)-1-propyne | C3H5NO | 详情 | 详情 | |
(VIII) | 47157 | C29H32N2O11 | 详情 | 详情 |