(2R,4S,5R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2R,4S,5R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 155396-68-2
• Molecular Formula: C₃₂H₄₀N₂O₇S
• Molecular Weight: 596.745

Synonyms:(2R,4S,5R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property of (2R,4S,5R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

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SDS file from LookChem

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Technology Process of (2R,4S,5R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 8 articles about (2R,4S,5R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 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: 90.0%

[(1S,2R)-3-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-(4-methoxy-benzyloxy)-3-oxo-1-phenyl-propyl]-carbamic acid tert-butyl ester (155396-67-1) → (2R,4S,5R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester (155396-68-2)

Guidance literature:

With 4 A molecular sieve; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 14h;

DOI:10.1021/jo00085a004

Reference yield:

tert-butyl carbazate (4248-19-5) → (2R,4S,5R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester (155396-68-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 68 percent / HCOOH / methanol; H₂O / 21 h / 20 °C

2: 100 percent / K₂CO₃ / tetrahydrofuran / 12 h / Heating

3: 1.) LiN(Si(CH₃)3)2 / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 15 min

4: 90 percent / DDQ, 4 Angstroem molecular sieves / CH₂Cl₂ / 14 h / 20 °C

With formic acid; 4 A molecular sieve; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/jo00085a004

Reference yield:

(+)-camphorsultam (108448-77-7,124224-04-0) → (2R,4S,5R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester (155396-68-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / NaH / toluene / 1.) 20 deg C, 30 min, 2.) 20 deg C, 3 h

2: 1.) LiN(Si(CH₃)3)2 / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 15 min

3: 90 percent / DDQ, 4 Angstroem molecular sieves / CH₂Cl₂ / 14 h / 20 °C

With 4 A molecular sieve; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In dichloromethane; toluene;

DOI:10.1021/jo00085a004

upstream raw materials:

[(1S,2R)-3-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-(4-methoxy-benzyloxy)-3-oxo-1-phenyl-propyl]-carbamic acid tert-butyl ester

tert-butyl carbazate

(+)-camphorsultam

benzaldehyde

Downstream raw materials:

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid

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