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【结 构 式】

【分子编号】47942

【品名】(2S)-2-amino-N-[(3S,4R)-4-hydroxytetrahydro-3-furanyl]-4-methylpentanamide

【CA登记号】

【 分 子 式 】C10H20N2O3

【 分 子 量 】216.28048

【元素组成】C 55.53% H 9.32% N 12.95% O 22.19%

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:(VI)

Asymmetric opening of epoxide (I) with trimethylsilyl azide in the presence of (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamino-chromium as the chiral catalyst (Salen catalyst) provided the (3S,4R)-azido silyl alcohol (II). Removal of the silyl group with camphorsulfonic acid in MeOH and subsequent reduction of the azido moiety of (II) with hydrogen in the presence of Pd/C afforded the amino alcohol (III). Coupling of (III) with the mixed anhydride prepared from N-Cbz-leucine (IV) and isobutyric acid gave amide (V). The N-carbobenzoxy group of (V) was then removed by hydrogenolysis, yielding amine (VI), which was coupled with benzothiophene-2-carbonyl chloride (VII) to furnish the diamide (VIII). The secondary alcohol of (VIII) was finally oxidized to the target ketone using the Dess-Martin reagent in CH2Cl2.

1 Fenwick, A.E.; Ife, R.J.; Gribble, A.D.; Witherington, J.; Stevens, N.; Diastereoselective synthesis, activity and chiral stability of cyclic alkoxyketone inhibitors of cathepsin K. Bioorg Med Chem Lett 2001, 11, 2, 199.
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) 46598 3,6-dioxabicyclo[3.1.0]hexane C4H6O2 详情 详情
(II) 46599 [[(3R,4S)-4-azidotetrahydro-3-furanyl]oxy](trimethyl)silane; (3R,4S)-4-azidotetrahydro-3-furanyl trimethylsilyl ether C7H15N3O2Si 详情 详情
(III) 46601 (3R,4S)-4-aminotetrahydro-3-furanol C4H9NO2 详情 详情
(IV) 22839 tert-butyl 3-[((2S)-2-[[(benzyloxy)carbonyl]amino]-4-methylpentanoyl)amino]-4-hydroxy-1-pyrrolidinecarboxylate C23H35N3O6 详情 详情
(V) 47941 benzyl (1S)-1-([[(3S,4R)-4-hydroxytetrahydro-3-furanyl]amino]carbonyl)-3-methylbutylcarbamate C18H26N2O5 详情 详情
(VI) 47942 (2S)-2-amino-N-[(3S,4R)-4-hydroxytetrahydro-3-furanyl]-4-methylpentanamide C10H20N2O3 详情 详情
(VII) 47943 1-benzothiophene-2-carbonyl chloride 39827-11-7 C9H5ClOS 详情 详情
(VIII) 47944 N-[(1S)-1-([[(3S,4R)-4-hydroxytetrahydro-3-furanyl]amino]carbonyl)-3-methylbutyl]-1-benzothiophene-2-carboxamide C19H24N2O4S 详情 详情
Extended Information