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【结 构 式】

【分子编号】61806

【品名】{(5R)-3-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl methanesulfonate

【CA登记号】

【 分 子 式 】C18H29NO6SSi

【 分 子 量 】415.5829

【元素组成】C 52.02% H 7.03% N 3.37% O 23.1% S 7.72% Si 6.76%

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:(VII)

The intermediate benzaldehyde (XII) has been obtained as follows: The reduction of 4-nitrobenzaldehyde (I) with NaBH4 and NiCl2 gives 4-aminobenzyl alcohol (II), which is treated with benzyl chloroformate to yield the carbamate (III). The protection of the OH group of (III) with Tbdms-Cl affords the silyl ether (IV). The cyclization of (IV) with glycidyl butyrate (V) by means of BuLi provides the hydroxymethyl oxazolidinone (VI), which is treated with MsCl and TEA to give the mesylate (VII). The reaction of (VII) with NaN3 yields the azidomethyl compound (VIII), which is condensed with thioacetic acid (IX) to afford the acetamide (X). The cleavage of the Tbdms protecting group of (X) by means of TBAF provides the benzyl alcohol (XI), which is oxidized with PDC to furnish the target benzaldehyde intermediate (XII)

1 Selvakumar, N.; et al.; Synthesis and antibacterial activity of novel chalcone oxazolidinone hybrids. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-1323.
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) 18184 4-Nitrobenzaldehyde 555-16-8 C7H5NO3 详情 详情
(II) 34431 diallyl (2S)-2-isocyanatopentanedioate C12H15NO5 详情 详情
(III) 61803 benzyl 4-(hydroxymethyl)phenylcarbamate C15H15NO3 详情 详情
(IV) 61804 benzyl 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenylcarbamate C21H29NO3Si 详情 详情
(V) 18385 (2R)oxiranylmethyl butyrate;(R)-glycidyl butyrate 60456-26-0 C7H12O3 详情 详情
(VI) 61805 (5R)-3-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one C17H27NO4Si 详情 详情
(VII) 61806 {(5R)-3-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl methanesulfonate C18H29NO6SSi 详情 详情
(VIII) 61807 (5R)-5-(azidomethyl)-3-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]-1,3-oxazolidin-2-one C17H26N4O3Si 详情 详情
(IX) 12893 Ethanethioic S-acid C2H4OS 详情 详情
(X) 61808 N-({(5S)-3-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide C19H30N2O4Si 详情 详情
(XI) 61809 N-({(5S)-3-[4-(hydroxymethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide C13H16N2O4 详情 详情
(XII) 61812 N-{[(5S)-3-(4-formylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide C13H14N2O4 详情 详情
Extended Information