{(S)-1-[(S)-5-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-4,5-dihydro-isoxazol-3-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {(S)-1-[(S)-5-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-4,5-dihydro-isoxazol-3-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester
• CAS No.: 145679-60-3
• Molecular Formula: C₂₇H₃₇N₃O₆S
• Molecular Weight: 531.673

Synonyms:

Chemical Property of {(S)-1-[(S)-5-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-4,5-dihydro-isoxazol-3-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

Chemical Property:

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Safty Information:

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MSDS Files:

Useful:

Technology Process of {(S)-1-[(S)-5-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-4,5-dihydro-isoxazol-3-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

There total 3 articles about {(S)-1-[(S)-5-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-4,5-dihydro-isoxazol-3-yl]-2-phenyl-ethyl}-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:

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester (51987-73-6) → {(S)-1-[(S)-5-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-4,5-dihydro-isoxazol-3-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester (145679-60-3)

Guidance literature:

Multi-step reaction with 3 steps

1: DIBAL / toluene / 0.08 h / -78 °C

2: NH₂OH*HCl, Na₂CO₃

3: 1) NBS, pyridine, 2) NEt₃ / 1) THF, 2) toluene

With pyridine; N-Bromosuccinimide; hydroxylamine hydrochloride; diisobutylaluminium hydride; sodium carbonate; triethylamine; In toluene;

DOI:10.1016/S0040-4039(00)61782-3

Reference yield:

Boc-L-phenylalaninal (72155-45-4) → {(S)-1-[(S)-5-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-4,5-dihydro-isoxazol-3-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester (145679-60-3)

Guidance literature:

Multi-step reaction with 2 steps

1: NH₂OH*HCl, Na₂CO₃

2: 1) NBS, pyridine, 2) NEt₃ / 1) THF, 2) toluene

With pyridine; N-Bromosuccinimide; hydroxylamine hydrochloride; sodium carbonate; triethylamine;

DOI:10.1016/S0040-4039(00)61782-3

Reference yield:

acrylcamphorsultam (94594-91-9) + (S)-2-(tert-butoxycarbonylamino)-3-phenylpropanal oxime (145625-14-5,1033194-57-8) → 3-<(1S)-N-(tert-butyloxycarbonyl)amino-2-phenylethyl>-5-<(2R)-(bornane-10,2-sultamyl)-N-carbonyl>-(5R)-Δ2-isoxazoline (145625-20-3) + {(S)-1-[(S)-5-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-4,5-dihydro-isoxazol-3-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester (145679-60-3)

Guidance literature:

With pyridine; N-Bromosuccinimide; triethylamine; Yield given. Multistep reaction. Yields of byproduct given; 1) THF, 2) toluene;

DOI:10.1016/S0040-4039(00)61782-3

upstream raw materials:

acrylcamphorsultam

(S)-2-(tert-butoxycarbonylamino)-3-phenylpropanal oxime

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

Boc-L-phenylalaninal

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