[(1S,2S,5S)-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-(tert-butyldiphenylsilanyloxymethyl)-2,5-dimethylcyclohex-3-enyl]-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

Base Information

• Chemical Name: [(1S,2S,5S)-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-(tert-butyldiphenylsilanyloxymethyl)-2,5-dimethylcyclohex-3-enyl]-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]dec-4-yl)-methanone
• CAS No.: 427897-76-5
• Molecular Formula: C₄₅H₆₉NO₅SSi₂
• Molecular Weight: 792.284

Synonyms:[(1S,2S,5S)-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-(tert-butyldiphenylsilanyloxymethyl)-2,5-dimethylcyclohex-3-enyl]-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

Chemical Property of [(1S,2S,5S)-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-(tert-butyldiphenylsilanyloxymethyl)-2,5-dimethylcyclohex-3-enyl]-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of [(1S,2S,5S)-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-(tert-butyldiphenylsilanyloxymethyl)-2,5-dimethylcyclohex-3-enyl]-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

There total 9 articles about [(1S,2S,5S)-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-(tert-butyldiphenylsilanyloxymethyl)-2,5-dimethylcyclohex-3-enyl]-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]dec-4-yl)-methanone 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:

acrylcamphorsultam (94594-91-9) + (2Z,4E)-8-[(tert-butyldimethylsilyl)oxy]-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-methyl-2,4-octadiene (193292-38-5) → [(1R,2S,5S)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dimethyl-cyclohex-3-enyl]-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone + [(1S,2S,5S)-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-(tert-butyldiphenylsilanyloxymethyl)-2,5-dimethylcyclohex-3-enyl]-(10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]dec-4-yl)-methanone (427897-76-5)

Guidance literature:

With methylaluminum dichloride; In dichloromethane; at -78 - 0 ℃;

DOI:10.1021/ol025772+

Reference yield:

acrylcamphorsultam (94594-91-9) + (2Z,4E)-8-[(tert-butyldimethylsilyl)oxy]-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-methyl-2,4-octadiene (193292-38-5) → [(1S,2S,5S)-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-(tert-butyldiphenylsilanyloxymethyl)-2,5-dimethylcyclohex-3-enyl]-(10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]dec-4-yl)-methanone (427897-76-5) + [(1R,2S,5S)-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-(tert-butyldiphenylsilanyloxymethyl)-2,5-dimethylcyclohex-3-enyl]-(10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]dec-4-yl)-methanone

Guidance literature:

With methylaluminum dichloride; In hexane; dichloromethane; at -78 - 0 ℃; for 2h;

DOI:10.1016/S0040-4020(02)00656-7

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → [(1S,2S,5S)-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-(tert-butyldiphenylsilanyloxymethyl)-2,5-dimethylcyclohex-3-enyl]-(10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]dec-4-yl)-methanone (427897-76-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C

2.2: 98 percent / tetrahydrofuran; hexane / -78 - 0 °C

3.1: copper(I) iodide / tetrahydrofuran; diethyl ether / 0.33 h / 0 °C

3.2: tetrahydrofuran; diethyl ether / 0.25 h / -78 °C

4.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / -78 - 0 °C

4.2: 88 percent / tetrahydrofuran; toluene / -78 - 0 °C

5.1: methylaluminum dichloride / CH₂Cl₂; hexane / 2 h / -78 - 0 °C

With 2,6-dimethylpyridine; copper(l) iodide; n-butyllithium; methylaluminum dichloride; potassium hexamethylsilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 4.2: Wittig olefination / 5.1: Diels-Alder reaction;

DOI:10.1016/S0040-4020(02)00656-7

upstream raw materials:

acrylcamphorsultam

(2Z,4E)-8-[(tert-butyldimethylsilyl)oxy]-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-methyl-2,4-octadiene

pent-1-yn-5-ol

5-[tert-butyldimethylsilyloxy]pent-1-yne

Downstream raw materials:

(1S,2S,5S)-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-(tert-butyldiphenylsilanyloxymethyl)-2,5-dimethyl-3-cyclohexene-1-carboxaldehyde

(1S,2S,5S)-4-(tert-butyldiphenylsilanyloxymethyl)-1-hydroxy-2-(3-hydroxypropyl)-2,5-dimethyl-3-cyclohexene-1-carboxylic acid methyl ester

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