3-Oxazolidinecarboxylic acid, 2,2-dimethyl-4-[[4-[[(trifluoromethyl)sulfonyl]oxy]phenyl]methyl]-, 1,1-dimethylethyl ester, (4S)-

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Chemical Name:3-Oxazolidinecarboxylic acid, 2,2-dimethyl-4-[[4-[[(trifluoromethyl)sulfonyl]oxy]phenyl]methyl]-, 1,1-dimethylethyl ester, (4S)-
CAS No.:386207-30-3
Molecular Formula:C18H24F3NO6S
Molecular Weight:439.453
Hs Code.:

Synonyms:

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Chemical Property of 3-Oxazolidinecarboxylic acid, 2,2-dimethyl-4-[[4-[[(trifluoromethyl)sulfonyl]oxy]phenyl]methyl]-, 1,1-dimethylethyl ester, (4S)-

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Technology Process of 3-Oxazolidinecarboxylic acid, 2,2-dimethyl-4-[[4-[[(trifluoromethyl)sulfonyl]oxy]phenyl]methyl]-, 1,1-dimethylethyl ester, (4S)-

There total 1 articles about 3-Oxazolidinecarboxylic acid, 2,2-dimethyl-4-[[4-[[(trifluoromethyl)sulfonyl]oxy]phenyl]methyl]-, 1,1-dimethylethyl ester, (4S)- 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: 86.0%

: 358-23-6
trifluoromethylsulfonic anhydride

: 143817-58-7
N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(4-hydroxyphenyl)-1,3-oxazolidine

: 386207-30-3
2,2-dimethyl-4-(4-trifluoromethanesulfonyloxy-benzyl)-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/jo040254t

Reference yield:

: 386207-30-3
2,2-dimethyl-4-(4-trifluoromethanesulfonyloxy-benzyl)-oxazolidine-3-carboxylic acid tert-butyl ester

: 845884-30-2
4-(4-carboxymethyl-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 80 percent / Pd(PPh₃)4 / LiCl / tetrahydrofuran / 11 h / Heating

2.1: 9-BBN / tetrahydrofuran / 5 h / 0 - 20 °C

2.2: 94 percent / NaOH; H₂O₂ / tetrahydrofuran / 0 - 20 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

4.1: NaClO₂; KH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 12 h / 20 °C

With sodium chlorite; potassium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2-methyl-but-2-ene; Dess-Martin periodane; lithium chloride; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 1.1: Stille coupling / 4.1: Pinnick oxidation;
DOI:10.1021/jo040254t

Reference yield:

: 386207-30-3
2,2-dimethyl-4-(4-trifluoromethanesulfonyloxy-benzyl)-oxazolidine-3-carboxylic acid tert-butyl ester

: (S)-4-[4-((4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-ylmethyl)-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 80 percent / Pd(PPh₃)4 / LiCl / tetrahydrofuran / 11 h / Heating

2.1: 9-BBN / tetrahydrofuran / 5 h / 0 - 20 °C

2.2: 94 percent / NaOH; H₂O₂ / tetrahydrofuran / 0 - 20 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

4.1: NaClO₂; KH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 12 h / 20 °C

5.1: 93 percent / DCC; 4-DMAP / CH₂Cl₂ / 18 h / 20 °C

6.1: TiCl₄; TMEDA; Zn / PbCl₂ / CH₂Cl₂; tetrahydrofuran / 1 h / 60 °C

7.1: second-generation Grubbs catalyst / toluene / 3 h / 60 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; sodium chlorite; potassium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2-methyl-but-2-ene; N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; Dess-Martin periodane; dicyclohexyl-carbodiimide; zinc; lithium chloride; lead(II) chloride; In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol; 1.1: Stille coupling / 4.1: Pinnick oxidation;
DOI:10.1021/jo040254t