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【结 构 式】 
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【分子编号】58653 【品名】5-hydroxy-2,2-dimethyl-10-propyl-2H,8H-pyrano[2,3-f]chromen-8-one 【CA登记号】 |
【 分 子 式 】C17H18O4 【 分 子 量 】286.32752 【元素组成】C 71.31% H 6.34% O 22.35% |
合成路线1
该中间体在本合成路线中的序号：(VI)The reaction of 5,7-dihydroxy-4-propyl-2H-1-benzopyran-2-one (I) with TsCl (or MsCl) and pyridine gives the ditosylate (II), which is selectively desulfonated by means of TBAF in THF at 0 C to yield monotosylate (III). The cyclization of (III) with 3-chloro-3-methyl-1-butyne (IV) by means of K2CO3, Bu4N+I- and ZnCl2 in butanone/DMF affords the benzodipyran (V), which is detosylated with TBAF in THF at 20 C to provide the hydroxy derivative (VI). Finally, the OH group of (VI) is enantioselectively alkylated with the mixed carbonate ester (VII) by means of Pd2dba3 ,Cs2CO3 and a (S,S)-chiral ligand in THF to furnish the target chiral intermediate (VIII) (see scheme no. 20433103a, intermediate (XXVII)).
| 【1】 Fox, M.E.; et al.; A novel synthesis of 5-hydroxy-2,2-dimethyl-10-propyl-2H-pyrano[2,3-f]chromen-8-one. Tetrahedron Lett 2002, 43, 16, 2899. |
| 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) | 22405 | 5,7-dihydroxy-4-propyl-2H-chromen-2-one | C12H12O4 | 详情 | 详情 | |
| (II) | 58650 | 5-{[(4-methylphenyl)sulfonyl]oxy}-2-oxo-4-propyl-2H-chromen-7-yl 4-methylbenzenesulfonate | C26H24O8S2 | 详情 | 详情 | |
| (III) | 58651 | 5-hydroxy-2-oxo-4-propyl-2H-chromen-7-yl 4-methylbenzenesulfonate | C19H18O6S | 详情 | 详情 | |
| (IV) | 58652 | 2,2-dimethyl-8-oxo-10-propyl-2H,8H-pyrano[2,3-f]chromen-5-yl 4-methylbenzenesulfonate | C24H24O6S | 详情 | 详情 | |
| (V) | 22416 | 3-chloro-3-methyl-1-butyne | 1111-97-3 | C5H7Cl | 详情 | 详情 |
| (VI) | 58653 | 5-hydroxy-2,2-dimethyl-10-propyl-2H,8H-pyrano[2,3-f]chromen-8-one | C17H18O4 | 详情 | 详情 | |
| (VII) | 22426 | methyl (E)-2-methyl-2-butenyl carbonate | C7H12O3 | 详情 | 详情 | |
| (VIII) | 22428 | 5-[[(1S)-1,2-dimethyl-2-propenyl]oxy]-2,2-dimethyl-10-propyl-2H,8H-pyrano[2,3-f]chromen-8-one | C22H26O4 | 详情 | 详情 |