(2S,4S,5R,1'S)-4-methyl-2-(2'-methyl-oxiran-2-yl)-5-phenyl-3-(toluene-4''-sulfonyl)-oxazolidine

Base Information

Chemical Name:(2S,4S,5R,1'S)-4-methyl-2-(2'-methyl-oxiran-2-yl)-5-phenyl-3-(toluene-4''-sulfonyl)-oxazolidine
CAS No.:166189-47-5
Molecular Formula:C₂₀H₂₃NO₄S
Molecular Weight:373.473
Hs Code.:

Synonyms:(2S,4S,5R,1'S)-4-methyl-2-(2'-methyl-oxiran-2-yl)-5-phenyl-3-(toluene-4''-sulfonyl)-oxazolidine

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Chemical Property of (2S,4S,5R,1'S)-4-methyl-2-(2'-methyl-oxiran-2-yl)-5-phenyl-3-(toluene-4''-sulfonyl)-oxazolidine

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Technology Process of (2S,4S,5R,1'S)-4-methyl-2-(2'-methyl-oxiran-2-yl)-5-phenyl-3-(toluene-4''-sulfonyl)-oxazolidine

There total 4 articles about (2S,4S,5R,1'S)-4-methyl-2-(2'-methyl-oxiran-2-yl)-5-phenyl-3-(toluene-4''-sulfonyl)-oxazolidine 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: 77.0%

: 166189-46-4
(1'S,2''S,4''S,5''R)-toluene-4-sulfonic acid 2'-hydroxy-2'-[4''-methyl-5''-phenyl-3''-(toluene-4'''-sulfonyl)-oxazolidin-2''-yl]-propyl ester

: 166189-47-5
(2S,4S,5R,1'S)-4-methyl-2-(2'-methyl-oxiran-2-yl)-5-phenyl-3-(toluene-4''-sulfonyl)-oxazolidine

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 1h; Ambient temperature;
DOI:10.1016/S0040-4020(96)01087-3

Reference yield:

: 108591-33-9
N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide

: 166189-47-5
(2S,4S,5R,1'S)-4-methyl-2-(2'-methyl-oxiran-2-yl)-5-phenyl-3-(toluene-4''-sulfonyl)-oxazolidine

Guidance literature:: Multi-step reaction with 4 steps

1: 50.2 percent / methyl orthoformate, pyridinium tosylate / benzene / 4 h / Heating

2: OsCl₃, Me₃NO*2H₂O / acetone; H₂O / 1 h

3: 85 percent / triethylamine, 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / 0 - 20 °C

4: 77 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / 1 h / Ambient temperature

With dmap; osmium (III) chloride; trimethylamine-N-oxide; pyridinium p-toluenesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trimethyl orthoformate; In tetrahydrofuran; dichloromethane; water; acetone; benzene;
DOI:10.1016/S0040-4020(96)01087-3

Reference yield:

: 143738-96-9
(2S,4S,5R)-2-isopropenyl-4-methyl-5-phenyl-3-(toluene-4'-sulfonyl)-oxazolidine

: 166189-47-5
(2S,4S,5R,1'S)-4-methyl-2-(2'-methyl-oxiran-2-yl)-5-phenyl-3-(toluene-4''-sulfonyl)-oxazolidine

Guidance literature:: Multi-step reaction with 3 steps

1: OsCl₃, Me₃NO*2H₂O / acetone; H₂O / 1 h

2: 85 percent / triethylamine, 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / 0 - 20 °C

3: 77 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / 1 h / Ambient temperature

With dmap; osmium (III) chloride; trimethylamine-N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane; water; acetone;
DOI:10.1016/S0040-4020(96)01087-3