tert-butyl-(1R,2E,4E,6R)-6-methoxy-1-(((2R,4R,6R)-4-methoxy-6-(phenylthio)-tetrahydro-2H-pyran-2-yl)-3-methylnona-2,4,8-trienyloxy)diphenylsilane

Base Information

Chemical Name:tert-butyl-(1R,2E,4E,6R)-6-methoxy-1-(((2R,4R,6R)-4-methoxy-6-(phenylthio)-tetrahydro-2H-pyran-2-yl)-3-methylnona-2,4,8-trienyloxy)diphenylsilane
CAS No.:920018-66-2
Molecular Formula:C₃₉H₅₀O₄SSi
Molecular Weight:642.975
Hs Code.:

Synonyms:tert-butyl-(1R,2E,4E,6R)-6-methoxy-1-(((2R,4R,6R)-4-methoxy-6-(phenylthio)-tetrahydro-2H-pyran-2-yl)-3-methylnona-2,4,8-trienyloxy)diphenylsilane

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Chemical Property of tert-butyl-(1R,2E,4E,6R)-6-methoxy-1-(((2R,4R,6R)-4-methoxy-6-(phenylthio)-tetrahydro-2H-pyran-2-yl)-3-methylnona-2,4,8-trienyloxy)diphenylsilane

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Technology Process of tert-butyl-(1R,2E,4E,6R)-6-methoxy-1-(((2R,4R,6R)-4-methoxy-6-(phenylthio)-tetrahydro-2H-pyran-2-yl)-3-methylnona-2,4,8-trienyloxy)diphenylsilane

There total 22 articles about tert-butyl-(1R,2E,4E,6R)-6-methoxy-1-(((2R,4R,6R)-4-methoxy-6-(phenylthio)-tetrahydro-2H-pyran-2-yl)-3-methylnona-2,4,8-trienyloxy)diphenylsilane 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: 89.0%

: 920018-65-1
(4R,5E,7E,9R)-9-(tert-butyldiphenylsilanyloxy)-9-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)-7-methylnona-1,5,7-trien-4-ol

: 74-88-4
methyl iodide

: 920018-66-2
tert-butyl-(1R,2E,4E,6R)-6-methoxy-1-(((2R,4R,6R)-4-methoxy-6-(phenylthio)-tetrahydro-2H-pyran-2-yl)-3-methylnona-2,4,8-trienyloxy)diphenylsilane

Guidance literature:: With sodium hydride; In tetrahydrofuran; for 1.5h; Heating;
DOI:10.1021/ol062530r

Reference yield:

: 920018-57-1
(R)-4-((4R,5R)-5-((tert-butyldimethylsilanyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-methoxybutanal

: 920018-66-2
tert-butyl-(1R,2E,4E,6R)-6-methoxy-1-(((2R,4R,6R)-4-methoxy-6-(phenylthio)-tetrahydro-2H-pyran-2-yl)-3-methylnona-2,4,8-trienyloxy)diphenylsilane

Guidance literature:: Multi-step reaction with 14 steps

1.1: 87 percent / pyridinium p-toluenesulfonate / 12 h / Heating

2.1: 78 percent / imidazole; 4-N,N-dimethylaminopyridine / dimethylformamide / 12 h

3.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 5.5 h / 0 - 20 °C

4.1: 75 percent / pyridinium p-toluenesulfonate / methanol / 3 h / Heating

5.1: 47 percent / zinc iodide / 1,2-dichloro-ethane / 5 h / 0 - 20 °C

6.1: 99 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / cooling

7.1: 92 percent / toluene / 12 h / 100 °C

8.1: 91 percent / diisobutylaluminium hydride / toluene / -78 - 20 °C

9.1: 87 percent / dimethylsulfoxide; oxalyl chloride; triethylamine / 1.75 h / cooling

10.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C

10.2: 83 percent / tetrahydrofuran / 1 h / 0 - 20 °C

11.1: 99 percent / diisobutylaluminium hydride / toluene / 1 h / -78 °C

12.1: 90 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / 105 h / cooling

13.1: (+)-B-methoxydiisopinocampheylborane / diethyl ether / 1 h / 0 - 20 °C

13.2: diethyl ether / 3 h / -78 °C

13.3: 79 percent / hydrogen peroxide; sodium carbonate / diethyl ether

14.1: 89 percent / sodium hydride / tetrahydrofuran / 1.5 h / Heating

With (+)-Ipc₂BOMe; 1H-imidazole; 2,6-dimethylpyridine; dmap; oxalyl dichloride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; zinc(II) iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 6.1: Swern oxidation / 7.1: Wittig reaction / 9.1: Swern oxidation / 10.2: Wittig reaction;
DOI:10.1021/ol062530r

Reference yield:

: 920018-56-0
tert-butyl(((4R,5R)-5-((S)-2-methoxypent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)dimethylsilane

: 920018-66-2
tert-butyl-(1R,2E,4E,6R)-6-methoxy-1-(((2R,4R,6R)-4-methoxy-6-(phenylthio)-tetrahydro-2H-pyran-2-yl)-3-methylnona-2,4,8-trienyloxy)diphenylsilane

Guidance literature:: Multi-step reaction with 15 steps

1.1: ozone / CH₂Cl₂ / -78 °C

1.2: 95 percent / triphenylphosphine / CH₂Cl₂ / 0.5 h / -78 - 20 °C

2.1: 87 percent / pyridinium p-toluenesulfonate / 12 h / Heating

3.1: 78 percent / imidazole; 4-N,N-dimethylaminopyridine / dimethylformamide / 12 h

4.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 5.5 h / 0 - 20 °C

5.1: 75 percent / pyridinium p-toluenesulfonate / methanol / 3 h / Heating

6.1: 47 percent / zinc iodide / 1,2-dichloro-ethane / 5 h / 0 - 20 °C

7.1: 99 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / cooling

8.1: 92 percent / toluene / 12 h / 100 °C

9.1: 91 percent / diisobutylaluminium hydride / toluene / -78 - 20 °C

10.1: 87 percent / dimethylsulfoxide; oxalyl chloride; triethylamine / 1.75 h / cooling

11.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C

11.2: 83 percent / tetrahydrofuran / 1 h / 0 - 20 °C

12.1: 99 percent / diisobutylaluminium hydride / toluene / 1 h / -78 °C

13.1: 90 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / 105 h / cooling

14.1: (+)-B-methoxydiisopinocampheylborane / diethyl ether / 1 h / 0 - 20 °C

14.2: diethyl ether / 3 h / -78 °C

14.3: 79 percent / hydrogen peroxide; sodium carbonate / diethyl ether

15.1: 89 percent / sodium hydride / tetrahydrofuran / 1.5 h / Heating

With (+)-Ipc₂BOMe; 1H-imidazole; 2,6-dimethylpyridine; dmap; oxalyl dichloride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; triethylamine; zinc(II) iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 7.1: Swern oxidation / 8.1: Wittig reaction / 10.1: Swern oxidation / 11.2: Wittig reaction;
DOI:10.1021/ol062530r