【结 构 式】 |
【分子编号】26085 【品名】2-Lithiopropionic acid lithium salt 【CA登记号】 |
【 分 子 式 】C3H4Li2O2 【 分 子 量 】85.94556 【元素组成】C 41.93% H 4.69% Li 16.15% O 37.23% |
合成路线1
该中间体在本合成路线中的序号:(II)Hydroxyacid (III) was prepared by condensation of 5-phenylpentanal (I) with the dilithium anion of propionic acid (II). Cyclization of (III) upon treatment with dipyridyl disulfide and PPh3, and then with mercuric mesylate yielded an equimolar mixture of beta-lactones (IV) and (V), from which the desired cis isomer (IV) was isolated by flash chromatography. Subsequent ring opening of (IV) with the sodium salt of 4-methoxythiophenol (VI) provided carboxylic acid (VII). This was converted to acid the corresponding chloride by means of oxalyl chloride and then condensed with O-(trimethylsilyl)hydroxylamine to produce hydroxamic acid (VIII). Finally, sulfide oxidation of (VIII) with Oxone furnished the target sulfonylhydroxamic acid.
【1】 Burns, C.J.; Groneberg, R.D.; Morrissette, M.M.; et al.; Dual inhibition of phosphodiesterase 4 and matrix metalloproteinases by an (arylsulfonyl)hydroxamic acid template. J Med Chem 1999, 42, 4, 541. |
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) | 25636 | 5-phenylpentanal | C11H14O | 详情 | 详情 | |
(II) | 26085 | 2-Lithiopropionic acid lithium salt | C3H4Li2O2 | 详情 | 详情 | |
(III) | 26086 | 3-hydroxy-2-methyl-7-phenylheptanoic acid | C14H20O3 | 详情 | 详情 | |
(IV) | 26087 | (3S,4R)-3-methyl-4-(4-phenylbutyl)-2-oxetanone | C14H18O2 | 详情 | 详情 | |
(V) | 26088 | (3R,4R)-3-methyl-4-(4-phenylbutyl)-2-oxetanone | C14H18O2 | 详情 | 详情 | |
(VI) | 25639 | 4-methoxyphenylhydrosulfide; 4-methoxybenzenethiol | 34320-82-6 | C7H8OS | 详情 | 详情 |
(VII) | 26089 | (2S,3R)-3-[(4-methoxyphenyl)sulfanyl]-2-methyl-7-phenylheptanoic acid | C21H26O3S | 详情 | 详情 | |
(VIII) | 26090 | (2S,3R)-N-hydroxy-3-[(4-methoxyphenyl)sulfanyl]-2-methyl-7-phenylheptanamide | C21H27NO3S | 详情 | 详情 |