(R,E)-4-(tert-butyldiphenylsilanyloxy)-4-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)-2-methylbut-2-enal

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Chemical Name:(R,E)-4-(tert-butyldiphenylsilanyloxy)-4-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)-2-methylbut-2-enal
CAS No.:920018-62-8
Molecular Formula:C₃₃H₄₀O₄SSi
Molecular Weight:560.83
Hs Code.:

Synonyms:(R,E)-4-(tert-butyldiphenylsilanyloxy)-4-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)-2-methylbut-2-enal

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Chemical Property of (R,E)-4-(tert-butyldiphenylsilanyloxy)-4-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)-2-methylbut-2-enal

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Technology Process of (R,E)-4-(tert-butyldiphenylsilanyloxy)-4-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)-2-methylbut-2-enal

There total 15 articles about (R,E)-4-(tert-butyldiphenylsilanyloxy)-4-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)-2-methylbut-2-enal 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: 87.0%

: 920018-78-6
(R,E)-4-(tert-butyldiphenylsilanyloxy)-4-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)-2-methylbut-2-en-1-ol

: 920018-62-8
(R,E)-4-(tert-butyldiphenylsilanyloxy)-4-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)-2-methylbut-2-enal

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; for 1.75h; cooling;
DOI:10.1021/ol062530r

Reference yield:

: 920018-58-2
(R)-1-((2R,4R,6R)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)ethane-1,2-diol

: 920018-62-8
(R,E)-4-(tert-butyldiphenylsilanyloxy)-4-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)-2-methylbut-2-enal

Guidance literature:: Multi-step reaction with 8 steps

1: 78 percent / imidazole; 4-N,N-dimethylaminopyridine / dimethylformamide / 12 h

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

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

4: 47 percent / zinc iodide / 1,2-dichloro-ethane / 5 h / 0 - 20 °C

5: 99 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / cooling

6: 92 percent / toluene / 12 h / 100 °C

7: 91 percent / diisobutylaluminium hydride / toluene / -78 - 20 °C

8: 87 percent / dimethylsulfoxide; oxalyl chloride; triethylamine / 1.75 h / cooling

With 1H-imidazole; 2,6-dimethylpyridine; dmap; oxalyl dichloride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; zinc(II) iodide; In methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 5: Swern oxidation / 6: Wittig reaction / 8: Swern oxidation;
DOI:10.1021/ol062530r

Reference yield:

: 191723-84-9
2-((4R,5R)-5-((tert-butyldimethylsilanyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde

: 920018-62-8
(R,E)-4-(tert-butyldiphenylsilanyloxy)-4-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)-2-methylbut-2-enal

Guidance literature:: Multi-step reaction with 12 steps

1.1: (-)-B-methoxydiisopinocampheylborane / hexane; diethyl ether / 0 - 20 °C

1.2: diethyl ether; hexane / 1 h / -100 - 0 °C

1.3: hydrogen peroxide; sodium hydroxide / diethyl ether; hexane

2.1: 26 mg / sodium hydride / tetrahydrofuran / 1.5 h / Heating

3.1: ozone / CH₂Cl₂ / -78 °C

3.2: 95 percent / triphenylphosphine / CH₂Cl₂ / 0.5 h / -78 - 20 °C

4.1: 87 percent / pyridinium p-toluenesulfonate / 12 h / Heating

5.1: 78 percent / imidazole; 4-N,N-dimethylaminopyridine / dimethylformamide / 12 h

6.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 5.5 h / 0 - 20 °C

7.1: 75 percent / pyridinium p-toluenesulfonate / methanol / 3 h / Heating

8.1: 47 percent / zinc iodide / 1,2-dichloro-ethane / 5 h / 0 - 20 °C

9.1: 99 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / cooling

10.1: 92 percent / toluene / 12 h / 100 °C

11.1: 91 percent / diisobutylaluminium hydride / toluene / -78 - 20 °C

12.1: 87 percent / dimethylsulfoxide; oxalyl chloride; triethylamine / 1.75 h / cooling

With (-)-B-methoxydiisopinocamphenylborane; 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; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 9.1: Swern oxidation / 10.1: Wittig reaction / 12.1: Swern oxidation;
DOI:10.1021/ol062530r