2-Benzenesulfonylmethyl-3-[3-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-4-methoxy-pyridine

Base Information

• Chemical Name: 2-Benzenesulfonylmethyl-3-[3-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-4-methoxy-pyridine
• CAS No.: 211758-61-1
• Molecular Formula: C₂₄H₃₅NO₄SSi
• Molecular Weight: 461.698
• Mol file: 211758-61-1.mol

Synonyms:2-Benzenesulfonylmethyl-3-[3-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-4-methoxy-pyridine

Chemical Property of 2-Benzenesulfonylmethyl-3-[3-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-4-methoxy-pyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Benzenesulfonylmethyl-3-[3-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-4-methoxy-pyridine

There total 10 articles about 2-Benzenesulfonylmethyl-3-[3-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-4-methoxy-pyridine 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:

2-methyl-4-nitropyridine N-oxide (5470-66-6) → 2-Benzenesulfonylmethyl-3-[3-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-4-methoxy-pyridine (211758-61-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 84 percent / PCl₃ / CHCl₃ / 40 h / Ambient temperature

2: 50 percent / NaOH / dimethylsulfoxide / 0.5 h / 15 - 20 °C

3: 83 percent / methanol / Ambient temperature

4: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, then -78 to 0 deg C, 45 min, 2.) THF, hexane, 1.25 h

5: 94 percent / Na/Hg, Na₂HPO₄ / methanol / 2.5 h / Ambient temperature

6: 89 percent / OsO₄, NaIO₄ / tetrahydrofuran / 7 h / 0 - 20 °C

7: 81 percent / tetrahydrofuran / 4.5 h / -50 - 20 °C

8: 82 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 48 h / Ambient temperature

9: 100 percent / m-CPBA / CH₂Cl₂ / 2 h / -78 °C

10: 1.) p-TsCl, Et₃N / 1.) CH₂Cl₂, -50 deg C to room temp., overnight, 2.) DMF, room temp., 18 h

With dmap; sodium hydroxide; sodium periodate; disodium hydrogenphosphate; sodium amalgam; osmium(VIII) oxide; n-butyllithium; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; phosphorus trichloride; In tetrahydrofuran; methanol; dichloromethane; chloroform; dimethyl sulfoxide;

DOI:10.1021/jo9801770

Reference yield:

2-methyl-4-nitro-pyridine (13508-96-8) → 2-Benzenesulfonylmethyl-3-[3-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-4-methoxy-pyridine (211758-61-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 50 percent / NaOH / dimethylsulfoxide / 0.5 h / 15 - 20 °C

2: 83 percent / methanol / Ambient temperature

3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, then -78 to 0 deg C, 45 min, 2.) THF, hexane, 1.25 h

4: 94 percent / Na/Hg, Na₂HPO₄ / methanol / 2.5 h / Ambient temperature

5: 89 percent / OsO₄, NaIO₄ / tetrahydrofuran / 7 h / 0 - 20 °C

6: 81 percent / tetrahydrofuran / 4.5 h / -50 - 20 °C

7: 82 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 48 h / Ambient temperature

8: 100 percent / m-CPBA / CH₂Cl₂ / 2 h / -78 °C

9: 1.) p-TsCl, Et₃N / 1.) CH₂Cl₂, -50 deg C to room temp., overnight, 2.) DMF, room temp., 18 h

With dmap; sodium hydroxide; sodium periodate; disodium hydrogenphosphate; sodium amalgam; osmium(VIII) oxide; n-butyllithium; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jo9801770

Reference yield:

3-Benzenesulfonylmethyl-2-methyl-4-nitro-pyridine (88912-66-7) → 2-Benzenesulfonylmethyl-3-[3-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-4-methoxy-pyridine (211758-61-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 83 percent / methanol / Ambient temperature

2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, then -78 to 0 deg C, 45 min, 2.) THF, hexane, 1.25 h

3: 94 percent / Na/Hg, Na₂HPO₄ / methanol / 2.5 h / Ambient temperature

4: 89 percent / OsO₄, NaIO₄ / tetrahydrofuran / 7 h / 0 - 20 °C

5: 81 percent / tetrahydrofuran / 4.5 h / -50 - 20 °C

6: 82 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 48 h / Ambient temperature

7: 100 percent / m-CPBA / CH₂Cl₂ / 2 h / -78 °C

8: 1.) p-TsCl, Et₃N / 1.) CH₂Cl₂, -50 deg C to room temp., overnight, 2.) DMF, room temp., 18 h

With dmap; sodium periodate; disodium hydrogenphosphate; sodium amalgam; osmium(VIII) oxide; n-butyllithium; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo9801770

upstream raw materials:

sodium benzenesulfonate

3-[3-(tert-Butyl-dimethyl-silanyloxy)-pent-4-enyl]-4-methoxy-2-methyl-pyridine 1-oxide

2-methyl-4-nitro-pyridine

2-methyl-4-nitropyridine N-oxide

Downstream raw materials:

(4E,16E)-7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.0^8,13]tetracosa-1⁽²⁴⁾,4,8,10,12,16,20,22-octaene

2,2-Dimethyl-propionic acid 1-(2-{2-[(E)-6-(2-benzenesulfonylmethyl-4-methoxy-pyridin-3-yl)-hex-3-enyl]-4-methoxy-pyridin-3-yl}-ethyl)-allyl ester

2,2-Dimethyl-propionic acid 1-(2-{4-methoxy-2-[(E)-6-(4-methoxy-2-phenylsulfanylmethyl-pyridin-3-yl)-hex-3-enyl]-pyridin-3-yl}-ethyl)-allyl ester

C₃₆H₅₀N₂O₃SSi

Refernces