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【结 构 式】 
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【分子编号】37318 【品名】(2R)-2-[(2-naphthylsulfonyl)amino]-3-sulfanylpropionic acid 【CA登记号】 |
【 分 子 式 】C13H13NO4S2 【 分 子 量 】311.38256 【元素组成】C 50.15% H 4.21% N 4.5% O 20.55% S 20.6% |
合成路线1
该中间体在本合成路线中的序号：(IV)Condensation of S-(4-monomethoxytrityl)-L-cysteine (I) with 2-naphthalenesulfonyl chloride (II) under Schotten-Baumann conditions afforded sulfonamide (III). Cleavage of the trityl group of (III) by treatment with trifluoroacetic acid and triisopropylsilane gave thiol (IV), which was protected as the thiopyridyl derivative (V) using dithiodipyridine. Coupling of (V) with 4-amidinophenylalanyl piperidine (VI) by means of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide - HCl (EDC), 1-hydroxybenzotriazole (HOBt) and N-ethylmorpholine (NEM) furnished dipeptide (VII). The thiopyridyl group of (VII) was then deprotected by treatment with tributyl phosphine to afford thiol (VIII).
| 【1】 Buijsman, R.C.; van Boeckel, C.A.A.; van der Marel, G.A.; Basten, J.E.M.; van Dinther, T.G.; van Boom, J.H.; Design and synthesis of a novel synthetic NAPAP-pentasaccharide conjugate displaying a dual antithrombotic action. Bioorg Med Chem Lett 1999, 9, 14, 2013. |
| 【2】 Van Boeckel, C.A.A.; Basten, J.E.M.; Dreef-Tromp, C.M.; Buijsman, R.C. (Akzo Nobel N.V.; Universiteit Leiden); Antithrombotic cpds.. WO 9965934 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 22457 | 2,2'-Dithiodipyridine; 2-(2-pyridinyldisulfanyl)pyridine; 2,2'-Dipyridinyl disulfide | 2127-03-9 | C10H8N2S2 | 详情 | 详情 |
| (I) | 37316 | (2R)-2-amino-3-[[(4-methoxyphenyl)(diphenyl)methyl]sulfanyl]propionic acid | C23H23NO3S | 详情 | 详情 | |
| (II) | 27989 | 2-naphthalenesulfonyl chloride | 93-11-8 | C10H7ClO2S | 详情 | 详情 |
| (III) | 37317 | (2R)-3-[[(4-methoxyphenyl)(diphenyl)methyl]sulfanyl]-2-[(2-naphthylsulfonyl)amino]propionic acid | C33H29NO5S2 | 详情 | 详情 | |
| (IV) | 37318 | (2R)-2-[(2-naphthylsulfonyl)amino]-3-sulfanylpropionic acid | C13H13NO4S2 | 详情 | 详情 | |
| (V) | 37319 | (2R)-2-[(2-naphthylsulfonyl)amino]-3-(2-pyridinyldisulfanyl)propionic acid | C18H16N2O4S3 | 详情 | 详情 | |
| (VI) | 37320 | 4-[2-amino-3-oxo-3-(1-piperidinyl)propyl]benzenecarboximidamide | C15H22N4O | 详情 | 详情 | |
| (VII) | 37321 | (2R)-N-[1-[4-[amino(imino)methyl]benzyl]-2-oxo-2-(1-piperidinyl)ethyl]-2-[(2-naphthylsulfonyl)amino]-3-(2-pyridinyldisulfanyl)propanamide | C33H36N6O4S3 | 详情 | 详情 | |
| (VIII) | 37322 | (2R)-N-[1-[4-[amino(imino)methyl]benzyl]-2-oxo-2-(1-piperidinyl)ethyl]-2-[(2-naphthylsulfonyl)amino]-3-sulfanylpropanamide | C28H33N5O4S2 | 详情 | 详情 |