【结 构 式】 |
【分子编号】45530 【品名】(2R,3S)-1-amino-3-(dibenzylamino)-4-phenyl-2-butanol 【CA登记号】 |
【 分 子 式 】C24H28N2O 【 分 子 量 】360.4992 【元素组成】C 79.96% H 7.83% N 7.77% O 4.44% |
合成路线1
该中间体在本合成路线中的序号:(IV)The reaction of N,N-dibenzyl-L-alaninal (I) with nitromethane, catalyzed by the chiral ammonium salt (II) and KF in THF gives the chiral nitroalcohol (III), which is reduced with NiCl2 and NaBH4 to yield the aminoalcohol (IV). The condensation of (IV) with isobutyraldehyde (V) affords the Schiff base (VI), which is reduced with NaBH4 to provide the secondary amine (VII). The reaction of (VII) with 4-nitrobenzenesulfonyl chloride (VIII) and TEA in dichloromethane furnishes the sulfonamide (IX), which is deprotected by hydrogenation with H2 over Pd/C in methanol, giving the diamino compound (X). Finally, this compound is condensed with 3(S)-tetrahydrofuryl (N-oxysuccinimidyl) carbonate (XI) by means of TEA in dichloromethane to afford the target carbamate.
【1】 Corey, E.J.; Zhang, F.-Y.; Re- and si-face-selective nitroaldol reactions catalyzed by a rigid chiral quaternary ammonium salt: A highly stereoselective synthesis of the HIV protease inhibitor amprenavir (Vertex 478). Angew Chem. Int Ed Engl 1999, 38, 13-14, 1931. |
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) | 37936 | (2S)-2-(dibenzylamino)-3-phenylpropanal | C23H23NO | 详情 | 详情 | |
(II) | 45528 | 1-(9-anthrylmethyl)-2-[(benzyloxy)(4-quinolinyl)methyl]-5-vinyl-1-azoniabicyclo[2.2.2]octane fluoride | C41H39FN2O | 详情 | 详情 | |
(III) | 45529 | (2R,3S)-3-(dibenzylamino)-1-nitro-4-phenyl-2-butanol | C24H26N2O3 | 详情 | 详情 | |
(IV) | 45530 | (2R,3S)-1-amino-3-(dibenzylamino)-4-phenyl-2-butanol | C24H28N2O | 详情 | 详情 | |
(V) | 13226 | 2-Methylpropanal; Isobutyraldehyde | 78-84-2 | C4H8O | 详情 | 详情 |
(VI) | 45531 | (2R,3S)-3-(dibenzylamino)-1-[[(E)-2-methylpropylidene]amino]-4-phenyl-2-butanol | C28H34N2O | 详情 | 详情 | |
(VII) | 37940 | (2R,3S)-3-(dibenzylamino)-1-(isobutylamino)-4-phenyl-2-butanol | C28H36N2O | 详情 | 详情 | |
(VIII) | 15809 | 4-nitrobenzenesulfonyl chloride | 98-74-8 | C6H4ClNO4S | 详情 | 详情 |
(IX) | 45532 | N-[(2R,3S)-3-(dibenzylamino)-2-hydroxy-4-phenylbutyl]-N-isobutyl-4-nitrobenzenesulfonamide | C34H39N3O5S | 详情 | 详情 | |
(X) | 45533 | 4-amino-N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-isobutylbenzenesulfonamide | C20H29N3O3S | 详情 | 详情 | |
(XI) | 39664 | 1-([[(3S)tetrahydro-3-furanyloxy]carbonyl]oxy)-2,5-pyrrolidinedione | C9H11NO6 | 详情 | 详情 |