【结 构 式】 |
【分子编号】64236 【品名】(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid 【CA登记号】 |
【 分 子 式 】C11H19NO5 【 分 子 量 】245.2756 【元素组成】C 53.87% H 7.81% N 5.71% O 32.62% |
合成路线1
该中间体在本合成路线中的序号:(I)The protected serine derivative (I) is converted into the corresponding Weinreb amide (II) upon coupling with N,O-dimethyl hydroxylamine in the presence of CBr4/PPh3. Reaction of (II) with 4-(benzyloxy)phenylmagnesium iodide (III) affords ketone (IV). Subsequent acidic cleavage of the protecting groups of (IV) leads to the hydroxy amino ketone (V). This is then acylated by oleoyl chloride (VI) to furnish amide (VII). Phosphitylation of the primary alcohol group of (VII) with di-tert-butyl N,N-diisopropylphosphoramidite, followed by oxidation with H2O2 gives rise to phosphate ester (VIII). The tert-butyl groups of (VIII) are finally cleaved by means of trifluoroacetic acid in CH2Cl2 to provide the title compound.
【1】 Heasley, B.H.; MacDonald, T.L.; Lynch, K.R.; Synthesis and biological evaluation of lysophosphatidic acid (LPA) antagonists. 225th ACS Natl Meet (March 23 2003, New Orleans) 2003, Abst MEDI 248. |
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) | 64236 | (4S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid | C11H19NO5 | 详情 | 详情 | |
(II) | 55202 | tert-butyl (4R)-4-{[methoxy(methyl)amino]carbonyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | C13H24N2O5 | 详情 | 详情 | |
(III) | 64237 | [4-(benzyloxy)phenyl](iodo)magnesium | C13H11IMgO | 详情 | 详情 | |
(IV) | 64238 | tert-butyl (4S)-4-[4-(benzyloxy)benzoyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | C24H29NO5 | 详情 | 详情 | |
(V) | 64239 | (2S)-2-amino-1-[4-(benzyloxy)phenyl]-3-hydroxy-1-propanone | C16H17NO3 | 详情 | 详情 | |
(VI) | 28280 | Oleoyl chloride; (E)-9-Octadecenoyl chloride | C18H33ClO | 详情 | 详情 | |
(VII) | 64240 | (Z)-N-[(1S)-2-[4-(benzyloxy)phenyl]-1-(hydroxymethyl)-2-oxoethyl]-9-octadecenamide | C34H49NO4 | 详情 | 详情 | |
(VIII) | 64241 | (2S)-3-[4-(benzyloxy)phenyl]-2-[(Z)-9-octadecenoylamino]-3-oxopropyl di(tert-butyl) phosphate | C42H66NO7P | 详情 | 详情 |