(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

Base Information

• Chemical Name: (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
• CAS No.: 447408-40-4
• Molecular Formula: C₄₁H₄₉IN₂O₅SSi
• Molecular Weight: 836.906

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 2 articles about (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 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: 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:

((Z)-5-Iodo-pent-4-enyl)-carbamic acid benzyl ester (447408-48-2) → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: 35 percent / trimethylsilyl iodide / acetonitrile / 0 °C

2: 65 percent / weakly acidic aluminum oxide / dimethylsulfoxide / 120 h / 20 °C

With aluminum oxide; trimethylsilyl iodide; In dimethyl sulfoxide; acetonitrile; 2: Michael addition;

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

Reference yield: 100.0%

(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) → (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[6.2.2.02,7]dodecan-3-one (447408-42-6)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃;

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

upstream raw materials:

(Z)-5-Iodo-pent-4-enylamine

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

((Z)-5-Iodo-pent-4-enyl)-carbamic acid benzyl ester

Downstream raw materials:

(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

C₄₁H₅₂N₂O₅SSi

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