8a-allyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methylene-2-(toluene-4-sulfonyl)-3,4,4a,8a-tetrahydro-2H,5H-isoquinoline-1,6-dione

Base Information

• Chemical Name: 8a-allyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methylene-2-(toluene-4-sulfonyl)-3,4,4a,8a-tetrahydro-2H,5H-isoquinoline-1,6-dione
• CAS No.: 447408-38-0
• Molecular Formula: C₃₆H₃₉NO₅SSi
• Molecular Weight: 625.861
• Mol file: 447408-38-0.mol

Synonyms:8a-allyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methylene-2-(toluene-4-sulfonyl)-3,4,4a,8a-tetrahydro-2H,5H-isoquinoline-1,6-dione

Chemical Property of 8a-allyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methylene-2-(toluene-4-sulfonyl)-3,4,4a,8a-tetrahydro-2H,5H-isoquinoline-1,6-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8a-allyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methylene-2-(toluene-4-sulfonyl)-3,4,4a,8a-tetrahydro-2H,5H-isoquinoline-1,6-dione

There total 1 articles about 8a-allyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methylene-2-(toluene-4-sulfonyl)-3,4,4a,8a-tetrahydro-2H,5H-isoquinoline-1,6-dione 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:

8a-allyl-4-(tert-butyl-diphenyl-silanyloxy)-5-dimethylaminomethyl-2-(toluene-4-sulfonyl)-3,4,4a,8a-tetrahydro-2H,5H-isoquinoline-1,6-dione → 8a-allyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methylene-2-(toluene-4-sulfonyl)-3,4,4a,8a-tetrahydro-2H,5H-isoquinoline-1,6-dione (447408-38-0)

Guidance literature:

With silica gel; chromatography;

DOI:10.1002/1521-3773(20020503)41:9<1581::AID-ANIE1581>3.0.CO;2-F

Reference yield: 65.0%

(Z)-5-Iodo-pent-4-enylamine (447408-39-1) + 8a-allyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methylene-2-(toluene-4-sulfonyl)-3,4,4a,8a-tetrahydro-2H,5H-isoquinoline-1,6-dione (447408-38-0) → (1S,2S,6R,7S,8R)-2-Allyl-6-(tert-butyl-diphenyl-silanyloxy)-10-((Z)-5-iodo-pent-4-enyl)-4-(toluene-4-sulfonyl)-4,10-diaza-tricyclo[6.2.2.02,7]dodecane-3,12-dione (447408-40-4) + (1R,2S,6R,7S,8S)-2-Allyl-6-(tert-butyl-diphenyl-silanyloxy)-10-((Z)-5-iodo-pent-4-enyl)-4-(toluene-4-sulfonyl)-4,10-diaza-tricyclo[6.2.2.02,7]dodecane-3,12-dione

Guidance literature:

With aluminum oxide; In dimethyl sulfoxide; at 20 ℃; for 120h;

DOI:10.1002/1521-3773(20020503)41:9<1581::AID-ANIE1581>3.0.CO;2-F

Reference yield:

8a-allyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methylene-2-(toluene-4-sulfonyl)-3,4,4a,8a-tetrahydro-2H,5H-isoquinoline-1,6-dione (447408-38-0) → C41H50N2O5SSi

Guidance literature:

Multi-step reaction with 5 steps

1.1: 65 percent / weakly acidic aluminum oxide / dimethylsulfoxide / 120 h / 20 °C

2.1: 100 percent / NaBH₄ / methanol / 0 °C

3.1: tetrahydrofuran / 20 °C

4.1: H₂O / ethyl acetate

4.2: Pd(dppf)Cl₂; Tl₂CO₃; AsPh₃ / tetrahydrofuran; dimethylformamide

5.1: 72 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one

With aluminum oxide; sodium tetrahydroborate; water; Dess-Martin periodane; In tetrahydrofuran; methanol; dimethyl sulfoxide; ethyl acetate; 1.1: Michael addition / 4.2: Suzuki reaction;

DOI:10.1002/1521-3773(20020503)41:9<1581::AID-ANIE1581>3.0.CO;2-F

Downstream raw materials:

(1S,2S,6R,7S,8R)-2-Allyl-6-(tert-butyl-diphenyl-silanyloxy)-10-((Z)-5-iodo-pent-4-enyl)-4-(toluene-4-sulfonyl)-4,10-diaza-tricyclo[6.2.2.0^2,7]dodecane-3,12-dione

C₄₁H₅₂N₂O₅SSi

(1S,2S,6R,7S,8R,12S)-2-Allyl-6-(tert-butyl-diphenyl-silanyloxy)-12-hydroxy-10-((Z)-5-iodo-pent-4-enyl)-4-(toluene-4-sulfonyl)-4,10-diaza-tricyclo[6.2.2.0^2,7]dodecan-3-one