(2'R,2''S,3''S,4R,5S,5''R)-(+)-<2'-(3'',5''-dimethyl-6''-oxotetrahydropyran-2''-yl)-1'-oxobutyl>-4-methyl-5-phenyloxazolidin-2-one

Base Information

• Chemical Name: (2'R,2''S,3''S,4R,5S,5''R)-(+)-<2'-(3'',5''-dimethyl-6''-oxotetrahydropyran-2''-yl)-1'-oxobutyl>-4-methyl-5-phenyloxazolidin-2-one
• CAS No.: 130514-52-2
• Molecular Formula: C₂₁H₂₇NO₅
• Molecular Weight: 373.449
• Mol file: 130514-52-2.mol

Synonyms:

Chemical Property of (2'R,2''S,3''S,4R,5S,5''R)-(+)-<2'-(3'',5''-dimethyl-6''-oxotetrahydropyran-2''-yl)-1'-oxobutyl>-4-methyl-5-phenyloxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'R,2''S,3''S,4R,5S,5''R)-(+)-<2'-(3'',5''-dimethyl-6''-oxotetrahydropyran-2''-yl)-1'-oxobutyl>-4-methyl-5-phenyloxazolidin-2-one

There total 11 articles about (2'R,2''S,3''S,4R,5S,5''R)-(+)-<2'-(3'',5''-dimethyl-6''-oxotetrahydropyran-2''-yl)-1'-oxobutyl>-4-methyl-5-phenyloxazolidin-2-one 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:

(4R,5S)-3-[(R)-2-((2S,3S,5R)-6-Hydroxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-butyryl]-4-methyl-5-phenyl-oxazolidin-2-one (130514-51-1) → (2'R,2''S,3''S,4R,5S,5''R)-(+)-<2'-(3'',5''-dimethyl-6''-oxotetrahydropyran-2''-yl)-1'-oxobutyl>-4-methyl-5-phenyloxazolidin-2-one (130514-52-2)

Guidance literature:

With silver carbonate; In toluene; for 1h; Yield given; Heating;

Reference yield:

4-methyl-5-phenyloxazolidin-2-one (77943-39-6) → (2'R,2''S,3''S,4R,5S,5''R)-(+)-<2'-(3'',5''-dimethyl-6''-oxotetrahydropyran-2''-yl)-1'-oxobutyl>-4-methyl-5-phenyloxazolidin-2-one (130514-52-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) butyllithium / 1.) THF/hexane, -78 deg C, 1 h, 2.) 1 h

2: 1.) 9-borabicyclo<3.3.1>non-9-yl trifluoromethanesulfonate, diisopropylethylamine / 1.) dichloromethane, 0 deg C, 0.5 h, 2a.) -78 deg C, 0.5 h, 2b.) RT, 1.5 h

3: 85 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 15 h / 25 °C

4: 1.) C₆H₁₃BH₂ (from borane-tetrahydrofuran and 2,3-dimethylbut-2-ene), 2.) aq. sodium bicarbonate, 30percent H₂O₂ / 1.) THF, 0 deg C, 5 h, 2.) 25 deg C, 12 h

5: 91 percent / oxalic acid / methanol / 1 h / 25 °C

6: N-methylmorpholine N-oxide, tris(triphenylphosphine)ruthenium(II) chloride / acetone / 3 h / 25 °C

7: Fetizon's reagent / toluene / 1 h / Heating

With dmap; n-butyllithium; tris(triphenylphosphine)ruthenium(II) chloride; C₆H₁₃BH₂ (from borane-tetrahydrofuran and 2,3-dimethylbut-2-ene); dihydrogen peroxide; oxalic acid; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; silver carbonate; 9-BBN triflate; In methanol; dichloromethane; acetone; toluene;

Reference yield:

(1S,2S)-2-amino-1-phenylpropanol (492-39-7,58550-13-3,757124-50-8) → (2'R,2''S,3''S,4R,5S,5''R)-(+)-<2'-(3'',5''-dimethyl-6''-oxotetrahydropyran-2''-yl)-1'-oxobutyl>-4-methyl-5-phenyloxazolidin-2-one (130514-52-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / potassium carbonate / toluene / 130 °C / Heating

2: 1.) butyllithium / 1.) THF/hexane, -78 deg C, 1 h, 2.) 1 h

3: 1.) 9-borabicyclo<3.3.1>non-9-yl trifluoromethanesulfonate, diisopropylethylamine / 1.) dichloromethane, 0 deg C, 0.5 h, 2a.) -78 deg C, 0.5 h, 2b.) RT, 1.5 h

4: 85 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 15 h / 25 °C

5: 1.) C₆H₁₃BH₂ (from borane-tetrahydrofuran and 2,3-dimethylbut-2-ene), 2.) aq. sodium bicarbonate, 30percent H₂O₂ / 1.) THF, 0 deg C, 5 h, 2.) 25 deg C, 12 h

6: 91 percent / oxalic acid / methanol / 1 h / 25 °C

7: N-methylmorpholine N-oxide, tris(triphenylphosphine)ruthenium(II) chloride / acetone / 3 h / 25 °C

8: Fetizon's reagent / toluene / 1 h / Heating

With dmap; n-butyllithium; tris(triphenylphosphine)ruthenium(II) chloride; C₆H₁₃BH₂ (from borane-tetrahydrofuran and 2,3-dimethylbut-2-ene); dihydrogen peroxide; oxalic acid; sodium hydrogencarbonate; potassium carbonate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; silver carbonate; 9-BBN triflate; In methanol; dichloromethane; acetone; toluene;

upstream raw materials:

(4R,5S)-3-[(R)-2-((2S,3S,5R)-6-Hydroxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-butyryl]-4-methyl-5-phenyl-oxazolidin-2-one

4-methyl-5-phenyloxazolidin-2-one

(1S,2S)-2-amino-1-phenylpropanol

(S)-(+)-2,4-dimethylpent-4-enal