(1R,2S)-1-phenyl-2-(N,2,4,6-tetramethylphenylsulfonamido)propyl (2R,3S)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-2-methylbutanoate

Base Information

Chemical Name:(1R,2S)-1-phenyl-2-(N,2,4,6-tetramethylphenylsulfonamido)propyl (2R,3S)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-2-methylbutanoate
CAS No.:1255212-57-7
Molecular Formula:C₃₀H₄₄N₂O₇S
Molecular Weight:576.755
Hs Code.:

Synonyms:(1R,2S)-1-phenyl-2-(N,2,4,6-tetramethylphenylsulfonamido)propyl (2R,3S)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-2-methylbutanoate

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Chemical Property of (1R,2S)-1-phenyl-2-(N,2,4,6-tetramethylphenylsulfonamido)propyl (2R,3S)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-2-methylbutanoate

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Technology Process of (1R,2S)-1-phenyl-2-(N,2,4,6-tetramethylphenylsulfonamido)propyl (2R,3S)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-2-methylbutanoate

There total 4 articles about (1R,2S)-1-phenyl-2-(N,2,4,6-tetramethylphenylsulfonamido)propyl (2R,3S)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-2-methylbutanoate 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:

: 123387-72-4
O-tert-butyl N-methyl-N-(2-oxoethyl)carbamate

: (1R,2S)-2-(N-methyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate

: 1255212-57-7
(1R,2S)-1-phenyl-2-(N,2,4,6-tetramethylphenylsulfonamido)propyl (2R,3S)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-2-methylbutanoate

: (1R,2S)-1-phenyl-2-(N,2,4,6-tetramethylphenylsulfonamido)propyl (2S,3S)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-2-methylbutanoate

Guidance literature:: (1R,2S)-2-(N-methyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate; With triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In dichloromethane; at -78 - -65 ℃; for 2.5h; Inert atmosphere;

O-tert-butyl N-methyl-N-(2-oxoethyl)carbamate; In dichloromethane; at -78 - -67 ℃; for 3.25h; Inert atmosphere;

With methanol; dihydrogen peroxide; In dichloromethane; at 0 - 20 ℃; for 1h; pH=7; optical yield given as %de; diastereoselective reaction; aq. buffer; Inert atmosphere;
DOI:10.1016/j.tet.2011.06.043

Reference yield:

: 123387-72-4
O-tert-butyl N-methyl-N-(2-oxoethyl)carbamate

: (1R,2S)-2-(N-methyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate

: 1-phenyl-2-(N,2,4,6-tetramethylphenylsulfonamido)propyl 4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-2-methylbutanoate

: 1255212-57-7
(1R,2S)-1-phenyl-2-(N,2,4,6-tetramethylphenylsulfonamido)propyl (2R,3S)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-2-methylbutanoate

Guidance literature:: (1R,2S)-2-(N-methyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate; With triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In dichloromethane; at -78 - -65 ℃; for 2.75h; Inert atmosphere;

O-tert-butyl N-methyl-N-(2-oxoethyl)carbamate; In dichloromethane; at -78 - -67 ℃; for 3.25h; optical yield given as %de; diastereoselective reaction;
DOI:10.1021/ja105119r

Reference yield:

: 57561-39-4
methyl(2-hydroxyethyl)carbamic acid tert-butyl ester

: 1-phenyl-2-(N,2,4,6-tetramethylphenylsulfonamido)propyl 4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-2-methylbutanoate

: 1255212-57-7
(1R,2S)-1-phenyl-2-(N,2,4,6-tetramethylphenylsulfonamido)propyl (2R,3S)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-2-methylbutanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 3 h / -70 °C

2.1: triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane / dichloromethane / 2.75 h / -78 - -65 °C / Inert atmosphere

2.2: 3.25 h / -78 - -67 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In dichloromethane;
DOI:10.1021/ja105119r