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【结 构 式】

【分子编号】10781

【品名】benzyl (2R,4aR,5aR,6S,7S,8R,9S,9aR,10aS)-6-[[(benzyloxy)carbonyl](methyl)amino]-2-methyl-4-oxo-4a,7,9-tris[(trimethylsilyl)methyl]decahydro-2H-pyrano[2,3-b][1,4]benzodioxin-8-yl(methyl)carbamate

【CA登记号】

【 分 子 式 】C42H66N2O8Si3

【 分 子 量 】811.25122

【元素组成】C 62.18% H 8.2% N 3.45% O 15.78% Si 10.39%

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)

A new synthesis of trospectomycin has been published: The protection of the amino groups of spectinomycin (I) with benzyl chloroformate gives compound (II), which is treated with trimethylsilylchloride to protect the hydroxyl groups yielding the fully protected compound (III). The reaction of (III) with tert-butyl hydroperoxide makes free the oxo group affording compound (IV), which is converted into the enol ester (V) with allyl chloroformate and LiHMDS. The trans-allylation of (V) in THF by means of Pd under Tsujii conditions gives the protected 3-butenyl derivative (VI), which is finally deprotected and simultaneously hydrogenated with H2 over Pd/Al2O3 in methanol-acetic acid.

1 Herrinton, P.M.; Hartley, W.M.; Klotz, K.L.; Oxidation and alkylation of spectinomycin derivatives: Synthesis of trospectomycin from spectinomycin. J Org Chem 1993, 58, 3, 678.
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) 10765 (2R,4aR,5aR,6S,7S,8R,9S,9aR,10aS)-4a,7,9-Trihydroxy-2-methyl-6,8-bis(methylamino)decahydro-4H-pyrano[2,3-b][1,4]benzodioxin-4-one C14H24N2O7 详情 详情
(II) 10766 benzyl (2R,4aR,5aR,6S,7S,8R,9S,9aR,10aS)-6-[[(benzyloxy)carbonyl](methyl)amino]-4a,7,9-trihydroxy-2-methyl-4-oxodecahydro-2H-pyrano[2,3-b][1,4]benzodioxin-8-yl(methyl)carbamate C30H36N2O11 详情 详情
(III) 10780 benzyl (2R,4aS,5aR,6S,7S,8R,9S,9aR,10aS)-6-[[(benzyloxy)carbonyl](methyl)amino]-2-methyl-4,4a,7,9-tetrakis[(trimethylsilyl)methyl]-4a,5a,6,7,8,9,9a,10a-octahydro-2H-pyrano[2,3-b][1,4]benzodioxin-8-yl(methyl)carbamate C46H76N2O7Si4 详情 详情
(IV) 10781 benzyl (2R,4aR,5aR,6S,7S,8R,9S,9aR,10aS)-6-[[(benzyloxy)carbonyl](methyl)amino]-2-methyl-4-oxo-4a,7,9-tris[(trimethylsilyl)methyl]decahydro-2H-pyrano[2,3-b][1,4]benzodioxin-8-yl(methyl)carbamate C42H66N2O8Si3 详情 详情
(V) 10782 (4aS,5aR,6S,7S,8R,9R,9aR,10aR)-6,8-bis[[(benzyloxy)carbonyl](methyl)amino]-2-methylene-4a,7,9-tris[(trimethylsilyl)methyl]-4a,5a,6,7,8,9,9a,10a-octahydro-2H-pyrano[2,3-b][1,4]benzodioxin-4-yl allyl carbonate C45H66N2O11Si3 详情 详情
(VI) 10783 benzyl (2R,4aS,5aR,6R,7R,8R,9S,9aS,10aS)-6-[[(benzyloxy)carbonyl](methyl)amino]-2-(3-butenyl)-4-oxo-4a,7,9-tris[(trimethylsilyl)oxy]decahydro-2H-pyrano[2,3-b][1,4]benzodioxin-8-yl(methyl)carbamate C40H58N2O10Si2 详情 详情
Extended Information