(3R,3aS,6R,6aS)-3,6-bis(benzyloxy)tetrahydrofuro[3,2-b]furan-2,5-dione -Drug Synthesis Database

【结构式】

【分子编号】25668

【品名】(3R,3aS,6R,6aS)-3,6-bis(benzyloxy)tetrahydrofuro[3,2-b]furan-2,5-dione

【CA登记号】

【分子式】C₂₀H₁₈O₆

【分子量】354.35932

【元素组成】C 67.79% H 5.12% O 27.09%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IV)

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.

参考文献中间体

合成目标

【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