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【结 构 式】

【分子编号】53933

【品名】beta-D-ribofuranose

【CA登记号】

【 分 子 式 】C5H10O5

【 分 子 量 】150.1314

【元素组成】C 40% H 6.71% O 53.28%

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:(I)

The chiral dihydroxypentenal acetonide (II) is obtained from D-ribose (I) by known methods. The condensation of (II) with ethyl diazoacetate (III) by means of SnCl2 in dichloromethane gives diazocompound (IV), which is submitted to an intramolecular cyclopropanation by means of Ts-N3 and CuI in refluxing toluene to afford the bicyclo[3,1,0] hexane derivative (V). The reduction of the ketone and ester groups of (V) by means of LiAlH4 in ethyl ether provides the bicyclo diol (VI), which is deprotected with HCl in THF/water to give the chiral tetrol (VII). Selective protection of the primary OH group of (VII) with trityl chloride, TEA and DMAP in DMF yields the trityl ether (VIII), which is oxidized with NaIO4 in THF/water to afford tritylated (1S,2R)-1,2-bis(hydroxymethyl)cyclopropanemethanol (IX). The acylation of (IX) with benzoyl chloride and pyridine provides the tritylated diester (X), which is finally deprotected with formic acid in ethyl ether to furnish the target intermediate (1S,2R)-bis(benzoyloxy)cyclopropanemethanol (XI) (see intermediate (XI) in scheme no. 19209002a of the current synthesis).

1 Gallos, J.K.; et al.; Carbocyclic nucleoside precursors by intramolecular cyclopropanation of sugar-derived diazo compounds. Tetrahedron Lett 2001, 42, 42, 7489.
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) 53933 beta-D-ribofuranose C5H10O5 详情 详情
(II) 53934 (4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolane-4-carbaldehyde n/a C8H12O3 详情 详情
(III) 31205 2-Diazoacetic acid ethyl ester C4H6N2O2 详情 详情
(IV) 53935   C12H16N2O5 详情 详情
(V) 53936 ethyl (3aR,3bR,5aR)-2,2-dimethyl-5-oxotetrahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxole-4a(3aH)-carboxylate C12H16O5 详情 详情
(VI) 53937 (3aR,3bR,4aS,5S,5aS)-4a-(hydroxymethyl)-2,2-dimethylhexahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-5-ol C10H16O4 详情 详情
(VII) 53938 (1S,2S,3R,4R,5R)-1-(hydroxymethyl)bicyclo[3.1.0]hexane-2,3,4-triol C7H12O4 详情 详情
(VIII) 53939 (1S,2S,3R,4R,5R)-1-[(trityloxy)methyl]bicyclo[3.1.0]hexane-2,3,4-triol C26H26O4 详情 详情
(IX) 53940 {(1R,2R)-2-(hydroxymethyl)-2-[(trityloxy)methyl]cyclopropyl}methanol C25H26O3 详情 详情
(X) 53941 {(1R,2S)-2-[(benzoyloxy)methyl]-2-[(trityloxy)methyl]cyclopropyl}methyl benzoate C39H34O5 详情 详情
(XI) 53929 [(1R,2S)-2-[(benzoyloxy)methyl]-2-(hydroxymethyl)cyclopropyl]methyl benzoate C20H20O5 详情 详情
Extended Information