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

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Chemical Name:(R,E)-methyl 4-(tert-butyldiphenylsilanyloxy)-4-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)-2-methylbut-2-enoate
CAS No.:920018-61-7
Molecular Formula:C₃₄H₄₂O₅SSi
Molecular Weight:590.856
Hs Code.:

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

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

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

There total 16 articles about (R,E)-methyl 4-(tert-butyldiphenylsilanyloxy)-4-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)-2-methylbut-2-enoate 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: 92.0%

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

: 21382-82-1
(carbethoxyethylidene)triphenylphosphorane

: 920018-61-7
(R,E)-methyl 4-(tert-butyldiphenylsilanyloxy)-4-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)-2-methylbut-2-enoate

Guidance literature:: In toluene; at 100 ℃; for 12h; Inert atmosphere;
DOI:10.1039/c2ob25766a

Reference yield:

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

: 920018-61-7
(R,E)-methyl 4-(tert-butyldiphenylsilanyloxy)-4-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)-2-methylbut-2-enoate

Guidance literature:: Multi-step reaction with 10 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

With (-)-B-methoxydiisopinocamphenylborane; 1H-imidazole; 2,6-dimethylpyridine; dmap; oxalyl dichloride; pyridinium p-toluenesulfonate; sodium 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;
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

: 920018-61-7
(R,E)-methyl 4-(tert-butyldiphenylsilanyloxy)-4-((2R,4R,6S)-4-methoxy-6-(phenylthio)tetrahydro-2H-pyran-2-yl)-2-methylbut-2-enoate

Guidance literature:: Multi-step reaction with 6 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

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; toluene; 5: Swern oxidation / 6: Wittig reaction;
DOI:10.1021/ol062530r