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【结 构 式】

【分子编号】64738

【品名】4-({[4-(methyloxy)phenyl]methyl}oxy)butanal

【CA登记号】

【 分 子 式 】C12H16O3

【 分 子 量 】208.25724

【元素组成】C 69.21% H 7.74% O 23.05%

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:(XII)

Mono-protection of 1,4-butanediol (XI) by means of 4-methoxybenzyl chloride, followed by Swern oxidation with DMSO/SO3-Pyr, leads to the aldehyde (XII). Condensation of (XII)with the boron enolate of the N-propionyl oxazolidinone (III) and subsequent silylation with tert-butyldimethylsilyl triflate furnishes the N-acyl oxoazolidinone (XIII), which is reduced by LiBH4 to the primary alcohol (XIV), which is then subjected to Swern oxidation to produce the aldehyde (XV). Further condensation of (XV) with acyl oxazolidinone (III) leads to adduct (XVI). The free hydroxyl group of (XVI) is alkylated with chloromethyl methyl ether to produce the O-methoxymethyl derivative (XVII), which under desilylation conditions with HF-pyridine cyclizes to the lactone (XVIII).

1 Choy, N.; Shin, Y.; Nguyen, P.Q.; Curran, D.P.; Balachandran, R.; Madiraju, C.; Day, B.W.; Simplified discodermolide analogues: Synthesis and biological evaluation of 4-epi-7-dehydroxy-14,16-didemethyl-(+)-discodermolides as microtubule-stabilizing agents. J Med Chem 2003, 46, 14, 2846.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(III) 25713 (4S)-4-benzyl-3-propionyl-1,3-oxazolidin-2-one C13H15NO3 详情 详情
(XI) 46190 (1R,2R,6S)-1-[(2S,3E)-2-[[tert-butyl(dimethyl)silyl]oxy]-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-butenyl]-2-hydroxy-2,6-dimethyl-7-octenyl methanesulfonate C26H47NO5S2Si 详情 详情
(XII) 64738 4-({[4-(methyloxy)phenyl]methyl}oxy)butanal C12H16O3 详情 详情
(XIII) 64739 3-[3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-methyl-6-({[4-(methyloxy)phenyl]methyl}oxy)hexanoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one C31H45NO6Si 详情 详情
(XIV) 64740 3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-methyl-6-({[4-(methyloxy)phenyl]methyl}oxy)-1-hexanol C21H38O4Si 详情 详情
(XV) 64741 3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-methyl-6-({[4-(methyloxy)phenyl]methyl}oxy)hexanal C21H36O4Si 详情 详情
(XVI) 64742   C34H51NO7Si 详情 详情
(XVII) 64743 3-[5-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2,4-dimethyl-3-{[(methyloxy)methyl]oxy}-8-({[4-(methyloxy)phenyl]methyl}oxy)octanoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one C36H55NO8Si 详情 详情
(XVIII) 64744 3,5-dimethyl-4-{[(methyloxy)methyl]oxy}-6-[3-({[4-(methyloxy)phenyl]methyl}oxy)propyl]tetrahydro-2H-pyran-2-one C20H30O6 详情 详情
Extended Information