5-[(1S,6R)-2-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2-(2-trimethylsilanyl-ethylsulfanyl)-cyclohexyl]-6-[1,3]dioxolan-2-yl-benzo[1,3]dioxole

Base Information

• Chemical Name: 5-[(1S,6R)-2-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2-(2-trimethylsilanyl-ethylsulfanyl)-cyclohexyl]-6-[1,3]dioxolan-2-yl-benzo[1,3]dioxole
• CAS No.: 118419-49-1
• Molecular Formula: C₃₃H₅₀O₇S₂Si₂
• Molecular Weight: 679.059
• Mol file: 118419-49-1.mol

Synonyms:5-[(1S,6R)-2-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2-(2-trimethylsilanyl-ethylsulfanyl)-cyclohexyl]-6-[1,3]dioxolan-2-yl-benzo[1,3]dioxole

Chemical Property of 5-[(1S,6R)-2-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2-(2-trimethylsilanyl-ethylsulfanyl)-cyclohexyl]-6-[1,3]dioxolan-2-yl-benzo[1,3]dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[(1S,6R)-2-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2-(2-trimethylsilanyl-ethylsulfanyl)-cyclohexyl]-6-[1,3]dioxolan-2-yl-benzo[1,3]dioxole

There total 1 articles about 5-[(1S,6R)-2-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2-(2-trimethylsilanyl-ethylsulfanyl)-cyclohexyl]-6-[1,3]dioxolan-2-yl-benzo[1,3]dioxole 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:

3-(tert-butyldimethylsilyloxy)-1-(phenylsulfonyl)cyclohexene (70810-37-6) + C10H9LiO4 (118419-48-0) + Toluene-4-thiosulfonic acid S-(2-trimethylsilanyl-ethyl) ester (114789-62-7) → 6-[(1S,6R)-2-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2-(2-trimethylsilanyl-ethylsulfanyl)-cyclohexyl]-benzo[1,3]dioxole-5-carbaldehyde (118419-50-4) + 5-[(1S,6R)-2-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2-(2-trimethylsilanyl-ethylsulfanyl)-cyclohexyl]-6-[1,3]dioxolan-2-yl-benzo[1,3]dioxole (118419-49-1)

Guidance literature:

Multistep reaction. Title compound not separated from byproducts; 1.) THF, ether, -78 deg C, 2.) 0 deg C;

DOI:10.1021/ja00184a082

Reference yield:

5-[(1S,6R)-2-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2-(2-trimethylsilanyl-ethylsulfanyl)-cyclohexyl]-6-[1,3]dioxolan-2-yl-benzo[1,3]dioxole (118419-49-1) → 6-[(1S,6R)-2-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2-(2-trimethylsilanyl-ethylsulfanyl)-cyclohexyl]-benzo[1,3]dioxole-5-carbaldehyde (118419-50-4)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 25 ℃; for 2h; Yield given;

DOI:10.1021/ja00184a082

Reference yield:

5-[(1S,6R)-2-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2-(2-trimethylsilanyl-ethylsulfanyl)-cyclohexyl]-6-[1,3]dioxolan-2-yl-benzo[1,3]dioxole (118419-49-1) → 6-{(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-6-[2-trimethylsilanyl-eth-(E)-ylidene]-cyclohexyl}-benzo[1,3]dioxole-5-carbaldehyde (118437-08-4)

Guidance literature:

Multi-step reaction with 5 steps

1: p-toluenesulfonic acid / acetone / 2 h / 25 °C

2: 93 percent / NaBH₄ / tetrahydrofuran; methanol / 0.17 h / Ambient temperature

3: 80 percent / MCPBA / CH₂Cl₂ / 1 h / 0 °C

4: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C to 0 deg C

5: 93 percent / MnO₂ / hexane / 1 h / Ambient temperature

With manganese(IV) oxide; sodium tetrahydroborate; n-butyllithium; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; acetone;

DOI:10.1021/ja00184a082

upstream raw materials:

3-(tert-butyldimethylsilyloxy)-1-(phenylsulfonyl)cyclohexene

C₁₀H₉LiO₄

Toluene-4-thiosulfonic acid S-(2-trimethylsilanyl-ethyl) ester

Downstream raw materials:

6-[(1S,6R)-2-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2-(2-trimethylsilanyl-ethylsulfanyl)-cyclohexyl]-benzo[1,3]dioxole-5-carbaldehyde

6-{(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-6-[2-trimethylsilanyl-eth-(E)-ylidene]-cyclohexyl}-benzo[1,3]dioxole-5-carbaldehyde

(6-{(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-6-[2-trimethylsilanyl-eth-(E)-ylidene]-cyclohexyl}-benzo[1,3]dioxol-5-yl)-methanol

(E)-3-(6-{(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-6-[2-trimethylsilanyl-eth-(E)-ylidene]-cyclohexyl}-benzo[1,3]dioxol-5-yl)-acrylic acid ethyl ester