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

【结构式】

【分子编号】21168

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

【CA登记号】

【分子式】C₂₅H₂₉NO₅

【分子量】423.509

【元素组成】C 70.9% H 6.9% N 3.31% O 18.89%

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：(XIV)

The hydroxy ketoester (XIII) (Scheme 24009402a), which is cyclized by means of NaOH in methanol/water affording the dihydropyranone (XIV). The reduction of the nitro group of (XIV) with hydrogen over Pd/C in THF gives the corresponding aniline (XV), which is finally amidated with 5-(trifluoromethyl)pyridine-2-sulfonyl chloride and pyridine in DMSO.

参考文献中间体

合成目标

【1】 Fors, K.S.; et al.; A convergent, scalable synthesis of HIV protease inhibitor PNU-140690. J Org Chem 1998, 63, 21, 7348.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XIII)	21167	methyl (5R)-5-hydroxy-2-[(1S)-1-(3-nitrophenyl)propyl]-3-oxo-5-phenethyloctanoate	C₂₆H₃₃NO₆	详情	详情
(XIV)	21168	(6R)-4-hydroxy-3-[(1R)-1-(3-nitrophenyl)propyl]-6-phenethyl-6-propyl-5,6-dihydro-2H-pyran-2-one	C₂₅H₂₉NO₅	详情	详情
(XV)	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
(XVI)	17237	5-(trifluoromethyl)-2-pyridinesulfonyl chloride	C₆H₃ClF₃NO₂S	详情	详情

合成路线2

该中间体在本合成路线中的序号： (XV)

参考文献中间体

合成目标

【1】 Trost BM, Andersen NG. 2002. Utilization of molybdenum-and palladium-catalyzed dynamic kinetic asymmetric transformations for the preparation of tertiary and quatemary stereogenic centers; a concise synthesis of tipranavir. J Am Chem Soc, 124 (48): 14320～14321

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	66865	methyl 3-(3-nitrophenyl)pent-4-enoate		C₁₂H₁₃NO₄	详情	详情
(V)	16524	bromo(vinyl)magnesium	1826-67-1	C₂H₃BrMg	详情	详情
(VII)	66867	1-propyl-1-vinylcyclopropane		C₈H₁₄	详情	详情
(IX)	66869	(E)-2-((4-methoxybenzyl)oxy)-2-styrylpentan-1-ol		C₂₁H₂₆O₃	详情	详情
(XII)	66872	(5S)-methyl 5-((4-methoxybenzyl)oxy)-2-((R)-1-(3-nitrophenyl)allyl)-3-oxo-5-phenethyloctanoate		C₃₄H₃₉NO₇	详情	详情
(XIII)	66873	(5S)-methyl 5-hydroxy-2-((R)-1-(3-nitrophenyl)allyl)-3-oxo-5-phenethyloctanoate		C₂₆H₃₁NO₆	详情	详情
(XIV)	66874	(S)-4-hydroxy-3-((R)-1-(3-nitrophenyl)allyl)-6-phenethyl-6-propyl-5,6-dihydro-2H-pyran-2-one		C₂₅H₂₇NO₅	详情	详情
(XV)	21168	(6R)-4-hydroxy-3-[(1R)-1-(3-nitrophenyl)propyl]-6-phenethyl-6-propyl-5,6-dihydro-2H-pyran-2-one		C₂₅H₂₉NO₅	详情	详情
(I)	66862	1-(3-nitrophenyl)prop-2-en-1-ol		C₉H₉NO₃	详情	详情
(II)	66863	tert-butyl (1-(3-nitrophenyl)allyl) carbonate		C₁₄H₁₇NO₅	详情	详情
(III)	66864	dimethyl 2-(1-(3-nitrophenyl)allyl)malonate		C₁₄H₁₅NO₆	详情	详情
(VI)	66866	1-chloropentan-2-one		C₅H₉ClO	详情	详情
(VIII)	66868	2-((4-methoxybenzyl)oxy)-2-vinylpentan-1-ol		C₁₅H₂₂O₃	详情	详情
(X)	66870	2-((4-methoxybenzyl)oxy)-2-phenethylpentan-1-ol		C₂₁H₂₈O₃	详情	详情
(XI)	66871	1-methoxy-4-(((3-phenethylhex-1-en-3-yl)oxy)methyl)benzene		C₂₂H₂₈O₂	详情	详情
(XVI)	66879	2-((4-methoxybenzyl)oxy)-2-phenethylpentanal		C₂₁H₂₆O₃	详情	详情

Extended Information