[(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

Base Information

• Chemical Name: [(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
• CAS No.: 155396-67-1
• Molecular Formula: C₃₂H₄₂N₂O₇S
• Molecular Weight: 598.761

Synonyms:[(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

Chemical Property of [(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

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Technology Process of [(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

There total 5 articles about [(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 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:

tert-butyl carbazate (4248-19-5) → [(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)

Guidance literature:

Multi-step reaction with 3 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

With formic acid; potassium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; water;

DOI:10.1021/jo00085a004

Reference yield:

(+)-camphorsultam (108448-77-7,124224-04-0) → [(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)

Guidance literature:

Multi-step reaction with 2 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

With sodium hydride; lithium hexamethyldisilazane; In toluene;

DOI:10.1021/jo00085a004

Reference yield:

benzaldehyde (100-52-7) → [(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)

Guidance literature:

Multi-step reaction with 3 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

With formic acid; potassium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; water;

DOI:10.1021/jo00085a004

upstream raw materials:

tert-butyl carbazate

(+)-camphorsultam

benzaldehyde

tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate

Downstream raw materials:

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

(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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