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【结 构 式】

【药物名称】

【化学名称】(2R,3R,4R,5R)-2,5-Di(benzyloxy)-3,4-dihydroxy-N,N'-bis[2(R)-hydroxyindan-1(S)-yl]hexanediamide

【CA登记号】

【 分 子 式 】C38H40N2O8

【 分 子 量 】652.7511

【开发单位】Linköping University(Originator), Stockholm University (Originator), Uppsala University (Originator)

【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY, HIV Protease Inhibitors

合成路线1

Oxidation of L-mannonic gamma-lactone (I) with aqueous nitric acid provided bislactone (II). Subsequent treatment of bislactone (II) with benzyl trichloroacetimidate (III) and trifluoromethanesulfonic acid furnished dibenzyl ether (IV). Then, nucleophilic opening of both lactone groups of (IV) with (1S,2R)-1-amino-2-indanol (V) in refluxing dichloromethane yielded the title bisamide.

1 Bjorsne, M.; Alterman, M.; Muhlman, A.; et al.; Design and synthesis of new potent C2-symmetric HIV-1 protease inhibitors. Use of L-mannaric acid as a peptidomimetic scaffold. J Med Chem 1998, 41, 20, 3782.
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) 25665 (3R,4S,5S)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxydihydro-2(3H)-furanone C6H10O6 详情 详情
(II) 25666 (3R,3aS,6R,6aS)-3,6-dihydroxytetrahydrofuro[3,2-b]furan-2,5-dione C6H6O6 详情 详情
(III) 25667 ethyl 2,2,2-trichloroethanimidoate 23213-96-9 C4H6Cl3NO 详情 详情
(IV) 25668 (3R,3aS,6R,6aS)-3,6-bis(benzyloxy)tetrahydrofuro[3,2-b]furan-2,5-dione C20H18O6 详情 详情
(V) 16239 (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol; Cis-(1S)-1-amino-2,3-dihydro-1H-inden-2-ol 126456-43-7 C9H11NO 详情 详情
Extended Information