(1R,3S,5R,6S,7S)-6-[(tert-butyldimethylsilyl)oxy]-8-[(1R)-1-(4-methoxyphenyl)ethyl]-4-oxa-8-azatricyclo[5.1.0.0^3,5]octan-2-one

Base Information

• Chemical Name: (1R,3S,5R,6S,7S)-6-[(tert-butyldimethylsilyl)oxy]-8-[(1R)-1-(4-methoxyphenyl)ethyl]-4-oxa-8-azatricyclo[5.1.0.0^3,5]octan-2-one
• CAS No.: 1560848-54-5
• Molecular Formula: C₂₁H₃₁NO₄Si
• Molecular Weight: 389.567

Synonyms:(1R,3S,5R,6S,7S)-6-[(tert-butyldimethylsilyl)oxy]-8-[(1R)-1-(4-methoxyphenyl)ethyl]-4-oxa-8-azatricyclo[5.1.0.0^3,5]octan-2-one

Chemical Property of (1R,3S,5R,6S,7S)-6-[(tert-butyldimethylsilyl)oxy]-8-[(1R)-1-(4-methoxyphenyl)ethyl]-4-oxa-8-azatricyclo[5.1.0.0^3,5]octan-2-one

Chemical Property:

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Technology Process of (1R,3S,5R,6S,7S)-6-[(tert-butyldimethylsilyl)oxy]-8-[(1R)-1-(4-methoxyphenyl)ethyl]-4-oxa-8-azatricyclo[5.1.0.0^3,5]octan-2-one

There total 2 articles about (1R,3S,5R,6S,7S)-6-[(tert-butyldimethylsilyl)oxy]-8-[(1R)-1-(4-methoxyphenyl)ethyl]-4-oxa-8-azatricyclo[5.1.0.0^3,5]octan-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: 70.0%

(1R,5R,6S)-5-[(tert-butyldimethylsilyl)oxy]-7-[(1R)-1-(4-methoxyphenyl)ethyl]-7-azabicyclo[4.1.0]hept-3-en-2-one (1560848-51-2) → (1R,3S,5R,6S,7S)-6-[(tert-butyldimethylsilyl)oxy]-8-[(1R)-1-(4-methoxyphenyl)ethyl]-4-oxa-8-azatricyclo[5.1.0.03,5]octan-2-one (1560848-54-5) + (1R,3R,5S,6S,7S)-6-[(tert-butyldimethylsilyl)oxy]-8-[(1R)-1-(4-methoxyphenyl)ethyl]-4-oxa-8-azatricyclo-[5.1.0.03,5]octan-2-one (1560848-56-7)

Guidance literature:

With dihydrogen peroxide; N-benzyl-trimethylammonium hydroxide; In tetrahydrofuran; methanol; water; at 0 ℃; for 0.5h;

DOI:10.1021/jo402535j

Reference yield:

4-(tert-Butyl-dimethyl-silanyloxy)-2-iodo-cyclohex-2-enone (179949-73-6) → (1R,3S,5R,6S,7S)-6-[(tert-butyldimethylsilyl)oxy]-8-[(1R)-1-(4-methoxyphenyl)ethyl]-4-oxa-8-azatricyclo[5.1.0.03,5]octan-2-one (1560848-54-5) + (1R,3R,5S,6S,7S)-6-[(tert-butyldimethylsilyl)oxy]-8-[(1R)-1-(4-methoxyphenyl)ethyl]-4-oxa-8-azatricyclo-[5.1.0.03,5]octan-2-one (1560848-56-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1,10-Phenanthroline; caesium carbonate / toluene / 1 h / 96 °C

2.1: lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

2.2: 3 h / -78 °C / Inert atmosphere

3.1: dihydrogen peroxide; N-benzyl-trimethylammonium hydroxide / methanol; tetrahydrofuran; water / 0.5 h / 0 °C

With 1,10-Phenanthroline; dihydrogen peroxide; N-benzyl-trimethylammonium hydroxide; caesium carbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; water; toluene;

DOI:10.1021/jo402535j

Reference yield:

(1R,3S,5R,6S,7S)-6-[(tert-butyldimethylsilyl)oxy]-8-[(1R)-1-(4-methoxyphenyl)ethyl]-4-oxa-8-azatricyclo[5.1.0.03,5]octan-2-one (1560848-54-5) → LL-C10037α (93752-54-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogen azide / toluene / 0.33 h / 20 °C

2.1: triphenylphosphine / tetrahydrofuran / 2 h / 0 - 20 °C

2.2: 3 h / 20 °C

3.1: 5 h / 0 - 20 °C

4.1: water; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C

With hydrogen azide; tetrabutyl ammonium fluoride; water; triphenylphosphine; In tetrahydrofuran; toluene; 2.1: |Staudinger Azide Reduction / 2.2: |Staudinger Azide Reduction;

DOI:10.1021/jo402535j

upstream raw materials:

4-(tert-Butyl-dimethyl-silanyloxy)-2-iodo-cyclohex-2-enone

(1R,5R,6S)-5-[(tert-butyldimethylsilyl)oxy]-7-[(1R)-1-(4-methoxyphenyl)ethyl]-7-azabicyclo[4.1.0]hept-3-en-2-one

Downstream raw materials:

LL-C10037α

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