• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】32879

【品名】4-hydroxy-6-phenethyl-6-propyl-5,6-dihydro-2H-pyran-2-one

【CA登记号】

【 分 子 式 】C16H20O3

【 分 子 量 】260.333

【元素组成】C 73.82% H 7.74% O 18.44%

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:(III)

A new synthesis of PNU-140690 has been developed: The condensation of 1-phenyl-3-hexanone (I) with methyl acetoacetate (II) by means of NaH in THF, followed by cyclization gives the hydroxypyrone (III), which by condensation with 3-nitrobenzaldehyde (IV) by means of AlCl3 in THF yields the benzylidene-pyrone (V). The alkylation of (V) with Et3Al, CuBr-Me2S in THF affords intermediate (VI), which is reduced at the nitro group with H2 over Pd/C in methanol giving the racemic amine (VII). The optical resolution of the N-benzyloxycarbonyl derivative of (VII) with chiral HPLC yielded the desired (R,R)-enantiomer (VIII), which was finally sulfonated with 5-(trifluoromethyl)pyridine-2-sulfonyl chloride (IX) in pyridine/dichloromethane.

1 Turner, S.R.; Strohbach, J.W.; Tommasi, R.A.; Aristoff, P.A.; Johnson, P.D.; Skulnick, H.I.; Dolak, L.A.; Seest, E.P.; Tomich, P.K.; Bohanon, M.J.; Horng, M.M.; Lynn, J.C.; Chong, K.T.; Hinshaw, R.R.; Watenpaugh, K.D.; Janakiraman, M.N.; Thaisrivongs, S.; Tipranavir (PNU-140690): A potent, orally bioavailable nonpeptidic HIV protease inhibitor of the 5,6-dihydro-4-hydroxy-2-pyrone sulfonamide class. J Med Chem 1998, 41, 18, 3467.
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) 17233 1-phenyl-3-hexanone C12H16O 详情 详情
(II) 11791 methyl 3-oxobutanoate; Methyl acetoacetate 105-45-3 C5H8O3 详情 详情
(III) 32879 4-hydroxy-6-phenethyl-6-propyl-5,6-dihydro-2H-pyran-2-one C16H20O3 详情 详情
(IV) 12646 3-Nitrobenzaldehyde 99-61-6 C7H5NO3 详情 详情
(V) 32880 3-[(Z)-(3-nitrophenyl)methylidene]-6-phenethyl-6-propyldihydro-2H-pyran-2,4-dione C23H23NO5 详情 详情
(VI) 32881 4-hydroxy-3-[1-(3-nitrophenyl)propyl]-6-phenethyl-6-propyl-5,6-dihydro-2H-pyran-2-one C25H29NO5 详情 详情
(VII) 32882 3-[1-(3-aminophenyl)propyl]-4-hydroxy-6-phenethyl-6-propyl-5,6-dihydro-2H-pyran-2-one C25H31NO3 详情 详情
(VIII) 17236 (6R)-3-[(1R)-1-(3-aminophenyl)propyl]-4-hydroxy-6-phenethyl-6-propyl-5,6-dihydro-2H-pyran-2-one C25H31NO3 详情 详情
(IX) 17237 5-(trifluoromethyl)-2-pyridinesulfonyl chloride C6H3ClF3NO2S 详情 详情
Extended Information