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

Base Information

• Chemical Name: (1S,2'S,4'S,5'R)-2-iodo-1-<4'-methyl-5'-phenyl-3'-(toluene-4''-sulfonyl)-oxazolidin-2'-yl>-ethanol
• CAS No.: 143739-03-1
• Molecular Formula: C₁₉H₂₂INO₄S
• Molecular Weight: 487.358

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

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

Chemical Property:

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

There total 4 articles about (1S,2'S,4'S,5'R)-2-iodo-1-<4'-methyl-5'-phenyl-3'-(toluene-4''-sulfonyl)-oxazolidin-2'-yl>-ethanol 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: 53.0%

(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>-ethyl ester (143739-02-0) → (1S,2'S,4'S,5'R)-2-iodo-1-<4'-methyl-5'-phenyl-3'-(toluene-4''-sulfonyl)-oxazolidin-2'-yl>-ethanol (143739-03-1)

Guidance literature:

With sodium iodide; In acetone; Heating;

DOI:10.1039/c39920001027

Reference yield:

N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide (108591-33-9) → (1S,2'S,4'S,5'R)-2-iodo-1-<4'-methyl-5'-phenyl-3'-(toluene-4''-sulfonyl)-oxazolidin-2'-yl>-ethanol (143739-03-1)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridinium tosylate / benzene / Heating

2: 75 percent / OsCl₃, Me₃NO*2H₂O / acetone; H₂O / 3 h

3: 41 percent / pyridine / 1 h

4: 53 percent / NaI / acetone / 5 h / Heating

With pyridine; osmium (III) chloride; trimethylamine-N-oxide; pyridinium p-toluenesulfonate; sodium iodide; In water; acetone; benzene;

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

Reference yield:

(2S,4S,5R)-2-ethenyl-4-methyl-5-phenyl-3-p-toluenesulfonyloxazolidine (143738-99-2) → (1S,2'S,4'S,5'R)-2-iodo-1-<4'-methyl-5'-phenyl-3'-(toluene-4''-sulfonyl)-oxazolidin-2'-yl>-ethanol (143739-03-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / OsCl₃, Me₃NO*2H₂O / acetone; H₂O / 3 h

2: 41 percent / pyridine / 1 h

3: 53 percent / NaI / acetone / 5 h / Heating

With pyridine; osmium (III) chloride; trimethylamine-N-oxide; sodium iodide; In water; acetone;

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

upstream raw materials:

(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>-ethyl ester

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

(2S,4S,5R)-2-ethenyl-4-methyl-5-phenyl-3-p-toluenesulfonyloxazolidine

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

Downstream raw materials:

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

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