(1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one

Base Information

• Chemical Name: (1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one
• CAS No.: 188123-48-0
• Molecular Formula: C₃₃H₃₉NO₄Si
• Molecular Weight: 541.762

Synonyms:

Chemical Property of (1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one

There total 9 articles about (1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-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:

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + (1S,2R,6S,7S,8S)-5-((E)-But-2-enoyl)-8-(tert-butyl-diphenyl-silanyloxy)-3-oxa-5-aza-tricyclo[5.2.1.02,6]decan-4-one → (1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-3-oxa-5-aza-tricyclo[5.2.1.02,6]decan-4-one (188123-48-0)

Guidance literature:

With diethylaluminium chloride; In dichloromethane; at -78 ℃; for 0.5h; Yield given;

DOI:10.1016/S0040-4039(96)02402-1

Reference yield:

(+)-(1S,2R,6S,7R)-3-oxa-5-azatricyclo[5.2.1.02,6]dec-8-en-4-one (139240-75-8) → (1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-3-oxa-5-aza-tricyclo[5.2.1.02,6]decan-4-one (188123-48-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / Et₃N, DMAP / tetrahydrofuran / 1 h / Ambient temperature

2: 95 percent / tetrahydrofuran / 0.17 h / -78 °C

3: 63 percent / I₂ / CH₂Cl₂ / 7 h / Ambient temperature

4: 81 percent / AIBN, Bu₃SnH / benzene / 7 h / Heating

5: 100 percent / Cs₂CO₃ / methanol / 1.5 h / Ambient temperature

6: 99 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature

With dmap; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; sodium hydride; caesium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(96)02402-1

Reference yield:

(1S,3S,7S,8S,10R)-10-Hydroxy-4-oxa-6-aza-tricyclo[5.2.1.03,8]decan-5-one (188123-38-8) → (1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-3-oxa-5-aza-tricyclo[5.2.1.02,6]decan-4-one (188123-48-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(96)02402-1

upstream raw materials:

(1R,2R,3S,4S)-3-methylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid

(1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one

cyclopenta-1,3-diene

(+)-(1S,2R,6S,7R)-3-oxa-5-azatricyclo[5.2.1.0^2,6]dec-8-en-4-one

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