2-Benzyloxy-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-ethanone

Base Information

• Chemical Name: 2-Benzyloxy-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-ethanone
• CAS No.: 155487-36-8
• Molecular Formula: C₁₉H₂₅NO₄S
• Molecular Weight: 363.478

Synonyms:2-Benzyloxy-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-ethanone

Chemical Property of 2-Benzyloxy-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-ethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 2-Benzyloxy-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-ethanone

There total 1 articles about 2-Benzyloxy-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-ethanone 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: 97.0%

Benzyloxyacetyl chloride (19810-31-2) + (+)-camphorsultam (108448-77-7,124224-04-0) → 2-Benzyloxy-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-ethanone (155487-36-8)

Guidance literature:

With sodium hydride; In toluene; 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h;

DOI:10.1021/jo00085a004

Reference yield:

2-Benzyloxy-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-ethanone (155487-36-8) → (2R,3S)-2-benzyloxy-3-tert-butoxy-carbonylamino-3-phenylpropanoic acid (155396-65-9)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 70 percent / LiOH, H₂O₂ / tetrahydrofuran; H₂O / 15 h / 20 °C

With lithium hydroxide; dihydrogen peroxide; lithium hexamethyldisilazane; In tetrahydrofuran; water;

DOI:10.1021/jo00085a004

Reference yield:

2-Benzyloxy-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-ethanone (155487-36-8) → C56H61Cl6NO16 (1053738-36-5)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 70 percent / LiOH, H₂O₂ / tetrahydrofuran; H₂O / 15 h / 20 °C

3: 1.) DCC, 2.) DMAP / 1.) toluene, 20 deg C, 5 min, 2.) 20 deg C, 20 h

With dmap; lithium hydroxide; dihydrogen peroxide; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; water;

DOI:10.1021/jo00085a004

upstream raw materials:

Benzyloxyacetyl chloride

(+)-camphorsultam

Downstream raw materials:

(2R,3S)-2-benzyloxy-3-tert-butoxy-carbonylamino-3-phenylpropanoic acid

C₅₆H₆₁Cl₆NO₁₆

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