5-{4-Methoxy-2-[(E)-6-(4-methoxy-2-phenylsulfanylmethyl-pyridin-3-yl)-hex-3-enyl]-pyridin-3-yl}-pent-1-en-3-ol

Base Information

• Chemical Name: 5-{4-Methoxy-2-[(E)-6-(4-methoxy-2-phenylsulfanylmethyl-pyridin-3-yl)-hex-3-enyl]-pyridin-3-yl}-pent-1-en-3-ol
• CAS No.: 211758-66-6
• Molecular Formula: C₃₀H₃₆N₂O₃S
• Molecular Weight: 504.693

Synonyms:5-{4-Methoxy-2-[(E)-6-(4-methoxy-2-phenylsulfanylmethyl-pyridin-3-yl)-hex-3-enyl]-pyridin-3-yl}-pent-1-en-3-ol

Chemical Property of 5-{4-Methoxy-2-[(E)-6-(4-methoxy-2-phenylsulfanylmethyl-pyridin-3-yl)-hex-3-enyl]-pyridin-3-yl}-pent-1-en-3-ol

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Technology Process of 5-{4-Methoxy-2-[(E)-6-(4-methoxy-2-phenylsulfanylmethyl-pyridin-3-yl)-hex-3-enyl]-pyridin-3-yl}-pent-1-en-3-ol

There total 15 articles about 5-{4-Methoxy-2-[(E)-6-(4-methoxy-2-phenylsulfanylmethyl-pyridin-3-yl)-hex-3-enyl]-pyridin-3-yl}-pent-1-en-3-ol 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: 100.0%

C36H50N2O3SSi (211759-07-8) → 5-{4-Methoxy-2-[(E)-6-(4-methoxy-2-phenylsulfanylmethyl-pyridin-3-yl)-hex-3-enyl]-pyridin-3-yl}-pent-1-en-3-ol (211758-66-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 5.5h;

DOI:10.1021/jo9801770

Reference yield:

2-methyl-4-nitropyridine N-oxide (5470-66-6) → 5-{4-Methoxy-2-[(E)-6-(4-methoxy-2-phenylsulfanylmethyl-pyridin-3-yl)-hex-3-enyl]-pyridin-3-yl}-pent-1-en-3-ol (211758-66-6)

Guidance literature:

Multi-step reaction with 13 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: 95 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 6.5 h / Ambient temperature

9: 97 percent / m-CPBA / CH₂Cl₂ / 3 h / Ambient temperature

10: 1.) p-TsCl, Et₃N / 1.) CH₂Cl₂, -50 deg C, 5 h, 2.) DMF, room temp., 12 h

11: 1.) NaHMDS, 2.) Pd₂(dba)3*CHCl₃, 1,2-bis(diphenylphosphino)ethane / 1.) THF, -78 deg C, 70 min, 2.) THF, reflux, 4 h

12: 66 percent / Na/Hg, Na₂HPO₄ / methanol / 2 h / Ambient temperature

13: 100 percent / n-Bu₄NF / tetrahydrofuran / 5.5 h / 0 °C

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydroxide; sodium periodate; disodium hydrogenphosphate; sodium amalgam; osmium(VIII) oxide; n-butyllithium; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; 1,2-bis-(diphenylphosphino)ethane; phosphorus trichloride; In tetrahydrofuran; methanol; dichloromethane; chloroform; dimethyl sulfoxide;

DOI:10.1021/jo9801770

Reference yield:

2-methyl-4-nitro-pyridine (13508-96-8) → 5-{4-Methoxy-2-[(E)-6-(4-methoxy-2-phenylsulfanylmethyl-pyridin-3-yl)-hex-3-enyl]-pyridin-3-yl}-pent-1-en-3-ol (211758-66-6)

Guidance literature:

Multi-step reaction with 12 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: 95 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 6.5 h / Ambient temperature

8: 97 percent / m-CPBA / CH₂Cl₂ / 3 h / Ambient temperature

9: 1.) p-TsCl, Et₃N / 1.) CH₂Cl₂, -50 deg C, 5 h, 2.) DMF, room temp., 12 h

10: 1.) NaHMDS, 2.) Pd₂(dba)3*CHCl₃, 1,2-bis(diphenylphosphino)ethane / 1.) THF, -78 deg C, 70 min, 2.) THF, reflux, 4 h

11: 66 percent / Na/Hg, Na₂HPO₄ / methanol / 2 h / Ambient temperature

12: 100 percent / n-Bu₄NF / tetrahydrofuran / 5.5 h / 0 °C

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydroxide; sodium periodate; disodium hydrogenphosphate; sodium amalgam; osmium(VIII) oxide; n-butyllithium; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jo9801770

upstream raw materials:

C₃₆H₅₀N₂O₃SSi

2-methyl-4-nitro-pyridine

2-methyl-4-nitropyridine N-oxide

3-Benzenesulfonylmethyl-2-methyl-4-nitro-pyridine

Downstream raw materials:

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

(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

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