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【结 构 式】 
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【分子编号】42188 【品名】(2R)-2-amino-3-[[(2R)-2-amino-2-carboxyethyl]disulfanyl]propionic acid 【CA登记号】 |
【 分 子 式 】C6H12N2O4S2 【 分 子 量 】240.30436 【元素组成】C 29.99% H 5.03% N 11.66% O 26.63% S 26.69% |
合成路线1
该中间体在本合成路线中的序号：(I)The title compound may be prepared either by acetylation of L-cystine (I) or by oxidative dimerization of N-acetylcysteine (II).
| 【1】 Andersson, C.-M.A.; Bergstrand, S.H.A.; Hallberg, A.R.; Särnstrand, B.O.; Tunek, P.A.S. (AstraZeneca plc); The pharmacological use of certain cystine derivs.. EP 0463514; EP 0532595; EP 0727207; JP 1992230359; JP 1993507705; US 5441976; US 5780508; WO 9118594 . |
合成路线2
该中间体在本合成路线中的序号：(I)Reductive cleavage of L-cystine (I) with sodium in liquid ammonia produced cysteine, which was subsequently alkylated with 2-(N-benzyloxycarbonylamino)ethyl tosylate (II) to afford thioether (III). After protection of (III) as the N-Boc derivative (IV), sulfur oxidation by means of Oxone(R) produced sulfone (V). The benzyloxycarbonyl protecting group of (V) was then cleaved by transfer hydrogenolysis employing formic acid and palladium catalyst, and the resulting amine (VI) was converted to amidine (VIII) by reaction thioacetimidate (VII). The Boc protecting group of (VIII) was finally removed by acidic treatment.
| 【1】 Young, R.J.; et al.; Inhibition of inducible nitric oxide synthase by acetamidine derivatives of hetero-substituted lysine and homolysine. Bioorg Med Chem Lett 2000, 10, 6, 597. |
| 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) | 42188 | (2R)-2-amino-3-[[(2R)-2-amino-2-carboxyethyl]disulfanyl]propionic acid | C6H12N2O4S2 | 详情 | 详情 | |
| (II) | 42170 | 2-[[(benzyloxy)carbonyl]amino]ethyl 4-methylbenzenesulfonate | C17H19NO5S | 详情 | 详情 | |
| (III) | 42189 | (2R)-2-amino-3-[(2-[[(benzyloxy)carbonyl]amino]ethyl)sulfanyl]propionic acid | C13H18N2O4S | 详情 | 详情 | |
| (IV) | 42190 | (2R)-3-[(2-[[(benzyloxy)carbonyl]amino]ethyl)sulfanyl]-2-[(tert-butoxycarbonyl)amino]propionic acid | C18H26N2O6S | 详情 | 详情 | |
| (V) | 42191 | (2R)-3-[(2-[[(benzyloxy)carbonyl]amino]ethyl)sulfonyl]-2-[(tert-butoxycarbonyl)amino]propionic acid | C18H26N2O8S | 详情 | 详情 | |
| (VI) | 42192 | (2R)-3-[(2-aminoethyl)sulfonyl]-2-[(tert-butoxycarbonyl)amino]propionic acid | C10H20N2O6S | 详情 | 详情 | |
| (VII) | 42175 | 1-naphthylmethyl ethanimidothioate | C13H13NS | 详情 | 详情 | |
| (VIII) | 42193 | (2R)-2-[(tert-butoxycarbonyl)amino]-3-[[2-(ethanimidoylamino)ethyl]sulfonyl]propionic acid | C12H23N3O6S | 详情 | 详情 |