(S)-5-((tert-butyldimethylsilyl)oxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpentanamide

Base Information

Chemical Name:(S)-5-((tert-butyldimethylsilyl)oxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpentanamide
CAS No.:618096-58-5
Molecular Formula:C₂₂H₃₉NO₃Si
Molecular Weight:393.642
Hs Code.:

Synonyms:(S)-5-((tert-butyldimethylsilyl)oxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpentanamide

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Chemical Property of (S)-5-((tert-butyldimethylsilyl)oxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpentanamide

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Technology Process of (S)-5-((tert-butyldimethylsilyl)oxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpentanamide

There total 1 articles about (S)-5-((tert-butyldimethylsilyl)oxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpentanamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

: 78878-05-4
1-iodo-3-(tert-butyldimethylsilyloxy)propane

: 192060-67-6
(1R,2R)-(-)-pseudoephedrinepropionamide

: 618096-58-5
(S)-5-((tert-butyldimethylsilyl)oxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpentanamide

Guidance literature:: (1R,2R)-(-)-pseudoephedrinepropionamide; With n-butyllithium; diisopropylamine; lithium chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 1.66667h; Inert atmosphere;

1-iodo-3-(tert-butyldimethylsilyloxy)propane; In tetrahydrofuran; hexane; at 0 ℃; for 18h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ja5043462

Reference yield:

: 618096-58-5
(S)-5-((tert-butyldimethylsilyl)oxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpentanamide

: 529494-90-4
(2R,4R,5S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4R,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-5-methyl-octane-2,4-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 99 percent / LDA; NH₃*NH₃ / tetrahydrofuran; hexane / 2 h / 0 °C

2.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

3.1: Et₃N; c-Hex₂BCl / diethyl ether / 0.5 h / 0 °C

3.2: 99 percent / diethyl ether / 20 h / -78 - -30 °C

4.1: 99 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / 30 h / -35 - -15 °C

With dicyclohexylboron chloride; ammonia; Dess-Martin periodane; triethylamine; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetic acid; acetonitrile; 4.1: Evans-Saksena reduction;
DOI:10.1016/S0040-4020(03)00814-7

Reference yield:

: 618096-58-5
(S)-5-((tert-butyldimethylsilyl)oxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpentanamide

: (S)-8-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-1-{(2S,4R,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-5-methyl-octan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 99 percent / LDA; NH₃*NH₃ / tetrahydrofuran; hexane / 2 h / 0 °C

2.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

3.1: Et₃N; c-Hex₂BCl / diethyl ether / 0.5 h / 0 °C

3.2: 99 percent / diethyl ether / 20 h / -78 - -30 °C

With dicyclohexylboron chloride; ammonia; Dess-Martin periodane; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1016/S0040-4020(03)00814-7