(2R,3R)-(+)-N-methoxy-N,2-dimethyl-3-(p-toluenesulfonamido)-3-phenylpropanamide

Base Information

Chemical Name:(2R,3R)-(+)-N-methoxy-N,2-dimethyl-3-(p-toluenesulfonamido)-3-phenylpropanamide
CAS No.:943241-46-1
Molecular Formula:C₁₉H₂₄N₂O₄S
Molecular Weight:376.477
Hs Code.:

Synonyms:(2R,3R)-(+)-N-methoxy-N,2-dimethyl-3-(p-toluenesulfonamido)-3-phenylpropanamide

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Chemical Property of (2R,3R)-(+)-N-methoxy-N,2-dimethyl-3-(p-toluenesulfonamido)-3-phenylpropanamide

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Technology Process of (2R,3R)-(+)-N-methoxy-N,2-dimethyl-3-(p-toluenesulfonamido)-3-phenylpropanamide

There total 7 articles about (2R,3R)-(+)-N-methoxy-N,2-dimethyl-3-(p-toluenesulfonamido)-3-phenylpropanamide 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: 37.0%

: 1287731-48-9
(R)-(+)-N-methoxy-N-methyl-3-phenyl-3-(tosylamino)-propanamide

: 74-88-4
methyl iodide

: 943241-46-1
(2R,3R)-(+)-N-methoxy-N,2-dimethyl-3-(p-toluenesulfonamido)-3-phenylpropanamide

: 1287731-64-9
(2S,3R)-(+)-N-methoxy-N,2-dimethyl-3-phenyl-3-(tosylamino)propanamide

Guidance literature:: (R)-(+)-N-methoxy-N-methyl-3-phenyl-3-(tosylamino)-propanamide; With n-butyllithium; diisopropylamine; lithium chloride; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; hexane; tert-butyl methyl ether; at -78 - -50 ℃; for 2h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/jo2002352

Reference yield:

: 100-52-7
benzaldehyde

: 943241-46-1
(2R,3R)-(+)-N-methoxy-N,2-dimethyl-3-(p-toluenesulfonamido)-3-phenylpropanamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: 77 percent / Ti(OEt)4 / CH₂Cl₂ / cooling

2.1: LiHMDS / tetrahydrofuran / 2 h / -78 °C

2.2: tetrahydrofuran / -78 °C

3.1: HCl / methanol; diethyl ether / 0.5 h / 0 °C

4.1: Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 °C

With hydrogenchloride; dmap; triethylamine; lithium hexamethyldisilazane; titanium(IV) tetraethanolate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1021/ol0708166