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

Base Information

• Chemical Name: (2S,2'S,4'S,5'R)-2-<4'-methyl-5'-phenyl-3'-(toluene-4''-sulfonyl)-oxazolidin-2'-yl>-propane-1,2-diol
• CAS No.: 143754-70-5
• Molecular Formula: C₂₀H₂₅NO₅S
• Molecular Weight: 391.488
• Mol file: 143754-70-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide (108591-33-9) → (2S,2'S,4'S,5'R)-2-<4'-methyl-5'-phenyl-3'-(toluene-4''-sulfonyl)-oxazolidin-2'-yl>-propane-1,2-diol (143754-70-5)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With osmium (III) chloride; trimethylamine-N-oxide; pyridinium p-toluenesulfonate; trimethyl orthoformate; In water; acetone; benzene;

DOI:10.1016/S0040-4020(96)01087-3

Reference yield:

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

Guidance literature:

With osmium (III) chloride; trimethylamine-N-oxide; In water; acetone; for 1h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4020(96)01087-3

upstream raw materials:

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

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

Downstream raw materials:

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

(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

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