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

Base Information

• Chemical Name: (2S,4S,5R)-2-isopropenyl-4-methyl-5-phenyl-3-(toluene-4'-sulfonyl)-oxazolidine
• CAS No.: 143738-96-9
• Molecular Formula: C₂₀H₂₃NO₃S
• Molecular Weight: 357.474
• Mol file: 143738-96-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (2S,4S,5R)-2-isopropenyl-4-methyl-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: 55.0%

2-methylpropenal (78-85-3,25120-30-3) + N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide (108591-33-9) → (2S,4S,5R)-2-isopropenyl-4-methyl-5-phenyl-3-(toluene-4'-sulfonyl)-oxazolidine (143738-96-9)

Guidance literature:

With pyridinium p-toluenesulfonate; trimethyl orthoformate; In benzene; Heating;

DOI:10.1039/c39920001027

Reference yield: 80.0%

(2S,4S,5R)-2-isopropenyl-4-methyl-5-phenyl-3-(toluene-4'-sulfonyl)-oxazolidine (143738-96-9) → (2RS,2'S,4'S,5'R)-2-<4'-methyl-5'-phenyl-3'-(toluene-4''-sulfonyl)-oxazolidin-2'-yl>-propane-1,2-diol (143754-69-2,143754-70-5)

Guidance literature:

With osmium (III) chloride; trimethylamine-N-oxide; water; In acetone; at 25 ℃;

DOI:10.1039/c39920001027

Reference yield:

(2S,4S,5R)-2-isopropenyl-4-methyl-5-phenyl-3-(toluene-4'-sulfonyl)-oxazolidine (143738-96-9) → (2S,4S,5R,1'S)-4-methyl-2-(2'-methyl-oxiran-2-yl)-5-phenyl-3-(toluene-4''-sulfonyl)-oxazolidine (166189-47-5)

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

upstream raw materials:

2-methylpropenal

N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide

Downstream raw materials:

(2RS,2'S,4'S,5'R)-2-<4'-methyl-5'-phenyl-3'-(toluene-4''-sulfonyl)-oxazolidin-2'-yl>-propane-1,2-diol

(2S,2'S,4'S,5'R)-2-<4'-methyl-5'-phenyl-3'-(toluene-4''-sulfonyl)-oxazolidin-2'-yl>-propane-1,2-diol

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

(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