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

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Chemical Name:(S)-2-(tert-butyldiphenylsilanyloxy)-2-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)acetaldehyde
CAS No.:920018-77-5
Molecular Formula:C₃₀H₃₆O₄SSi
Molecular Weight:520.765
Hs Code.:

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

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

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

There total 14 articles about (S)-2-(tert-butyldiphenylsilanyloxy)-2-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)acetaldehyde 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: 99.0%

: 920018-60-6
(R)-2-(tert-butyldiphenylsilanyloxy)-2-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)ethanol

: 920018-77-5
(S)-2-(tert-butyldiphenylsilanyloxy)-2-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)acetaldehyde

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

Reference yield:

: 920018-59-3
(R)-2-(tert-butyldimethylsilanyloxy)-1-((2R,4R,6R)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)ethanol

: 920018-77-5
(S)-2-(tert-butyldiphenylsilanyloxy)-2-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)acetaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 5.5 h / 0 - 20 °C

2: 75 percent / pyridinium p-toluenesulfonate / methanol / 3 h / Heating

3: 47 percent / zinc iodide / 1,2-dichloro-ethane / 5 h / 0 - 20 °C

4: 99 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / cooling

With 2,6-dimethylpyridine; oxalyl dichloride; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; zinc(II) iodide; In methanol; dichloromethane; 1,2-dichloro-ethane; 4: Swern oxidation;
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

: 920018-77-5
(S)-2-(tert-butyldiphenylsilanyloxy)-2-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)acetaldehyde

Guidance literature:: Multi-step reaction with 5 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

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