(6R)-3-[(1R)-1-[3-(dibenzylamino)phenyl]propyl]-4-hydroxy-6-phenethyl-6-(1-propynyl)-5,6-dihydro-2H-pyran-2-one -Drug Synthesis Database

【结构式】

【分子编号】17240

【品名】(6R)-3-[(1R)-1-[3-(dibenzylamino)phenyl]propyl]-4-hydroxy-6-phenethyl-6-(1-propynyl)-5,6-dihydro-2H-pyran-2-one

【CA登记号】

【分子式】C₃₉H₃₉NO₃

【分子量】569.7436

【元素组成】C 82.22% H 6.9% N 2.46% O 8.42%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XVI)

2) The previously obtained dione (VIII) can also be condensed with 1-phenyl-4-pentyn-1-one (XIV) by means of Ti(OBu)Cl3 in dichloromethane as before yielding the unsaturated hydroxy-dione (XV), which is cyclized by means of potassium tert-butoxide in THF to afford the dihydropyrone (XVI). The hydrogenation of the triple bond of (XVI) with simultaneous debenzylation by means of H2 over Pd/C in methanol/ethyl acetate gives the previously obtained free amine derivative (XII).

参考文献中间体

合成目标

【1】 Graul, J.; Wroblewski, T.; Castañer, J.; PNU-140690. Drugs Fut 1998, 23, 2, 146.
【2】 Morris, J.K.; Phillips, G.; Judge, T.M.; et al.; Asymmetric syntheses and absolute stereochemistry of 5,6-dihydro-alpha-pyrones, a new class of potent HIV protease inhibitors. J Am Chem Soc 1997, 119, 15, 3627-8.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VIII)	17232	(2S)-2-[(1S)-1-[3-(dibenzylamino)phenyl]propyl]-1-[(4R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]-1,3-butanedione	C₃₆H₃₆N₂O₄	详情	详情
(XII)	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
(XIV)	17238	1-phenyl-4-hexyn-3-one	C₁₂H₁₂O	详情	详情
(XV)	17239	(2S,5R)-2-[(1S)-1-[3-(dibenzylamino)phenyl]propyl]-5-hydroxy-1-[(4R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]-5-phenethyl-6-octyne-1,3-dione	C₄₈H₄₈N₂O₅	详情	详情
(XVI)	17240	(6R)-3-[(1R)-1-[3-(dibenzylamino)phenyl]propyl]-4-hydroxy-6-phenethyl-6-(1-propynyl)-5,6-dihydro-2H-pyran-2-one	C₃₉H₃₉NO₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XVIII)

参考文献中间体

合成目标

【1】 Judge TM, Phillips G, Moms JK, et aL. 1997. A symmetric syntheses and absolute stereochemistry of 5,6-dihydro-α-pyrones, a new class of potent HIV proteese inhibitors. J Am Chem Soc, 119 (15): 3627～3628

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)	12173	(4S)-4-Phenyl-1,3-oxazolan-2-one; (4S)-4-Phenyl-2-oxazolidinone; (S)-(+)-4-Phenyl-2-oxazolidinone	99395-88-7	C₉H₉NO₂	详情	详情
(II)	17227	(4R)-3-[(E)-2-pentenoyl]-4-phenyl-1,3-oxazolan-2-one		C₁₄H₁₅NO₃	详情	详情
(III)	17228	N-(3-methylphenyl)-N,N-bis(trimethylsilyl)amine; trimethyl-N-(3-methylphenyl)-N-(trimethylsilyl)silanamine		C₁₃H₂₅NSi₂	详情	详情
(V)	17231	2-methoxy-2-methyl-1,3-dioxolane; methyl 2-methyl-1,3-dioxolan-2-yl ether		C₅H₁₀O₃	详情	详情
(VI)	17232	(2S)-2-[(1S)-1-[3-(dibenzylamino)phenyl]propyl]-1-[(4R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]-1,3-butanedione		C₃₆H₃₆N₂O₄	详情	详情
(XI)	66877	2-(1-(3-(dibenzylamino)phenyl)propyl)-5-hydroxy-1-(2-oxo-4-phenyloxazolidin-3-yl)-5-phenethyloctane-1,3-dione		C₄₈H₅₂N₂O₅	详情	详情
(IV)	17229	(4R)-3-((3S)-3-[3-[bis(trimethylsilyl)amino]phenyl]pentanoyl)-4-phenyl-1,3-oxazolan-2-one		C₂₆H₃₈N₂O₃Si₂	详情	详情
(VII)	10385	4-Heptanone; Dipropyl ketone	123-19-3	C₇H₁₄O	详情	详情
(VIII)	17233	1-phenyl-3-hexanone		C₁₂H₁₆O	详情	详情
(IX)	66878	2-(1-(3-(dibenzylamino)phenyl)propyl)-5-hydroxy-1-(2-oxo-4-phenyloxazolidin-3-yl)-5-propyloctane-1,3-dione		C₄₃H₅₀N₂O₅	详情	详情
(X)	17234	(2S,5R)-2-[(1S)-1-[3-(dibenzylamino)phenyl]propyl]-5-hydroxy-1-[(4R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]-5-phenethyl-1,3-octanedione		C₄₈H₅₂N₂O₅	详情	详情
(XII)	66875	3-(1-(3-(dibenzylamino)phenyl)propyl)-4-hydroxy-6,6-dipropyl-5,6-dihydro-2H-pyran-2-one		C₃₄H₄₁NO₃	详情	详情
(XIII)	17235	(6R)-3-[(1R)-1-[3-(dibenzylamino)phenyl]propyl]-4-hydroxy-6-phenethyl-6-propyl-5,6-dihydro-2H-pyran-2-one		C₃₉H₄₃NO₃	详情	详情
(XIV)	66876	N-(3-(1-(4-hydroxy-2-oxo-6,6-dipropyl-5,6-dihydro-2H-pyran-3-yl)propyl)phenyl)-5-(trifluoromethyl)pyridine-2-sulfonamide		C₂₆H₃₁F₃N₂O₅S	详情	详情
(XVI)	17238	1-phenyl-4-hexyn-3-one		C₁₂H₁₂O	详情	详情
(XVII)	17239	(2S,5R)-2-[(1S)-1-[3-(dibenzylamino)phenyl]propyl]-5-hydroxy-1-[(4R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]-5-phenethyl-6-octyne-1,3-dione		C₄₈H₄₈N₂O₅	详情	详情
(XVIII)	17240	(6R)-3-[(1R)-1-[3-(dibenzylamino)phenyl]propyl]-4-hydroxy-6-phenethyl-6-(1-propynyl)-5,6-dihydro-2H-pyran-2-one		C₃₉H₃₉NO₃	详情	详情
(XIX)	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

Extended Information