2-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxybenzaldehyde -Drug Synthesis Database

【结构式】

【分子编号】56675

【品名】2-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxybenzaldehyde

【CA登记号】

【分子式】C₁₄H₂₂O₃Si

【分子量】266.41238

【元素组成】C 63.12% H 8.32% O 18.02% Si 10.54%

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：(VIII)

In a different strategy, 3-methoxysalicylaldehyde (VII) was protected as the silyl ether (VIII) using t-butyldimethylsilyl chloride and Et3N. Wittig reaction of aldehyde (VIII) with (9-hydroxynonyl)triphenylphosphonium bromide (IX) afforded olefin (X). This was alternatively prepared by addition of Grignard reagent (XI) to the aldehyde (VIII) to give carbinol (XII), which was further subjected to dehydration and acetal hydrolysis under acidic conditions to afford (X). Catalytic hydrogenation of olefin (X) furnished the 10-aryl decanol (XIII). The heptadecenyl side chain of (XVI) was then constructed by Swern oxidation of alcohol (XIII) to the corresponding aldehyde (XIV), followed by Wittig reaction with heptyltriphenylphosphonium bromide (XV). Desilylation of (XVI) with tetrabutylammonium fluoride gave the phenol precursor (VI), which was finally oxidized to the desired quinone by the same method as above.

参考文献中间体

合成目标

【1】 Wu, S.J.; Yang, Q.Z.; Chemical studies of Iris pallasii Fisch. var. chinensis Fisch.. Acta Chim Sin 1980, 38, 2, 156.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VI)	56674	2-[(Z)-10-heptadecenyl]-6-methoxyphenol		C₂₄H₄₀O₂	详情	详情
(VII)	12620	o-Vanillin; 2-Hydroxy-3-methoxybenzaldehyde	148-53-8	C₈H₈O₃	详情	详情
(VIII)	56675	2-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxybenzaldehyde		C₁₄H₂₂O₃Si	详情	详情
(IX)	56676	(9-hydroxynonyl)(triphenyl)phosphonium bromide		C₂₇H₃₄BrOP	详情	详情
(X)	56677	(Z)-10-(2-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxyphenyl)-9-decen-1-ol		C₂₃H₄₀O₃Si	详情	详情
(XI)	56678	bromo[9-(1-ethoxyethoxy)nonyl]magnesium		C₁₃H₂₇BrMgO₂	详情	详情
(XII)	56679	1-(2-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxyphenyl)-10-(1-ethoxyethoxy)-1-decanol		C₂₇H₅₀O₅Si	详情	详情
(XIII)	56680	10-(2-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxyphenyl)-1-decanol		C₂₃H₄₂O₃Si	详情	详情
(XIV)	56681	10-(2-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxyphenyl)decanal		C₂₃H₄₀O₃Si	详情	详情
(XV)	56682	heptyl(triphenyl)phosphonium bromide	13423-48-8	C₂₅H₃₀BrP	详情	详情
(XVI)	56683	tert-butyl{2-[(Z)-10-heptadecenyl]-6-methoxyphenoxy}dimethylsilane; tert-butyl(dimethyl)silyl 2-[(Z)-10-heptadecenyl]-6-methoxyphenyl ether		C₃₀H₅₄O₂Si	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

参考文献中间体

合成目标

【1】 Hu XD, Tu YQ, Zhang E,et aL 2006.Total synthesis of (±)-galanthamine. Org Lett,8(9): 1823--1825

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XI)	66422	(4aR,9bR)-9b-((1,3-dioxolan-2-yl)methyl)-6-methoxy-4,4a-dihydrodibenzo[b,d]furan-3(9bH)-one		C₁₇H₁₈O₅	详情	详情
(I)	11377	1,4-Dioxaspiro[4.5]decan-8-one	4746-97-8	C₈H₁₂O₃	详情	详情
(II)	66414	2,4,6-triisopropylbenzenesulfonohydrazide	39085-59-1	C₁₅H₂₆N₂O₂S	详情	详情
(III)	66415	2,4,6-triisopropyl-N'-(1,4-dioxaspiro[4.5]decan-8-ylidene)benzenesulfonohydrazide		C₂₃H₃₆N₂O₄S	详情	详情
(IV)	56675	2-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxybenzaldehyde		C₁₄H₂₂O₃Si	详情	详情
(V)	66416	(2-((tert-butyldimethylsilyl)oxy)-3-methoxyphenyl)(1,4-dioxaspiro[4.5]decan-8-yl)methanol		C₂₂H₃₆O₅Si	详情	详情
(VI)	66417	(7S,8R)-7-bromo-8-(2-((tert- butyldimethylsilyl)oxy)-3-methoxyphenyl)- 1,4-dioxaspiro[4.5]decane-8-carbaldehyde		C₂₂H₃₃BrO₅Si	详情	详情
(VII)	66418	(4aR,9bS)-6-methoxy-2,4,4a,9b-tetrahydro- 1H-spiro[dibenzo[b,d]furan-3,2'-[1,3] dioxolane]-9b-carbaldehyde		C₁₆H₁₈O₅	详情	详情
(VIII)	66419	(4aR,9bS)-6-methoxy-9b-((E)-2- methoxyvinyl)-2,4,4a,9b-tetrahydro-1H-spiro [dibenzo[b,d]furan-3,2'-[1,3]dioxolane]		C₁₈H₂₂O₅	详情	详情
(IX)	66420	(4aR,9bS)-9b-((1,3-dioxolan-2-yl)methyl)-6-methoxy-1,4,4a,9b-tetrahydrodibenzo[b,d]furan-3(2H)-one		C₁₇H₂₀O₅	详情	详情
(X)	66421	(((4aR,9bS)-9b-((1,3-dioxolan-2-yl)methyl)-6-methoxy-1,4,4a,9b-tetrahydrodibenzo[b,d]furan-3-yl)oxy)trimethylsilane		C₂₀H₂₈O₅Si	详情	详情
(XII)	66423	(3S,4aR,9bR)-9b-((1,3-dioxolan-2-yl)methyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzo[b,d]furan-3-ol		C₁₇H₂₀O₅	详情	详情
(XIII)	66424	(5aR,7S,9aS)-7-hydroxy-4-methoxy-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-carbaldehyde		C₁₄H₁₄O₄	详情	详情
(XIV)	66425	(3S,4aR,9bS)-9b-formyl-6-methoxy-3,4,4a,9b-tetrahydrodibenzo[b,d]furan-3-yl acetate		C₁₆H₁₆O₅	详情	详情
(XV)	66426	(3S,4aR,9bR)-9b-(2-bromo-2-oxoethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzo[b,d]furan-3-yl acetate		C₁₇H₁₇BrO₅	详情	详情
(XVI)	66427	(3S,4aR,9bR)-6-methoxy-9b-(2-(methylamino)-2-oxoethyl)-3,4,4a,9b-tetrahydrodibenzo[b,d]furan-3-yl acetate		C₁₈H₂₁NO₅	详情	详情
(XVII)	66428	(4aR,6S,8aR)-6-hydroxy-3-methoxy-11-methyl-5,6,11,12-tetrahydro-4aH-benzo[2,3]benzofuro[4,3-cd]azepin-10(9H)-one		C₁₇H₁₉NO₄	详情	详情

Extended Information