(R)-(-)-2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-<(phenylthio)methyl>cyclobutanone

Base Information

Chemical Name:(R)-(-)-2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-<(phenylthio)methyl>cyclobutanone
CAS No.:154699-07-7
Molecular Formula:C₂₄H₃₂O₂SSi
Molecular Weight:412.668
Hs Code.:

Synonyms:(R)-(-)-2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-<(phenylthio)methyl>cyclobutanone

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Chemical Property of (R)-(-)-2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-<(phenylthio)methyl>cyclobutanone

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Technology Process of (R)-(-)-2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-<(phenylthio)methyl>cyclobutanone

There total 9 articles about (R)-(-)-2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-<(phenylthio)methyl>cyclobutanone 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: 96.0%

: 882-33-7
diphenyldisulfane

: 154800-89-2
2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-(hydroxymethyl)cyclobutanone

: 154699-07-7
(R)-(-)-2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-<(phenylthio)methyl>cyclobutanone

Guidance literature:: With tributylphosphine; In tetrahydrofuran; for 7h; Heating;
DOI:10.1021/jo00080a014

Reference yield:

: 57234-27-2
1-(methoxymethoxy)-3-methylbenzene

: 154699-07-7
(R)-(-)-2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-<(phenylthio)methyl>cyclobutanone

Guidance literature:: Multi-step reaction with 9 steps

1: 80 percent / t-BuLi / diethyl ether; hexane / 0 °C / 1.) 2 h, 2.) 1 h

2: 94 percent / NaH / tris<2-(2-methoxyethoxy)ethyl>amine / tetrahydrofuran / 62 °C / 1.) 10 h, 2.) 1 h

3: 91 percent / EtSH, BF₃*Et₂O / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) -23 deg C, 1.5 h

4: 99 percent / n-Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 1 h / Ambient temperature

5: 85 percent / pyridine / 2 h / Ambient temperature

6: 86 percent / imidazole, DMAP / dimethylformamide / 10 h / 0 °C

7: 100 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -23 °C

8: 96 percent / m-CPBA / CH₂Cl₂ / 0.25 h / Ambient temperature

9: 96 percent / tri-n-butylphosphine / tetrahydrofuran / 7 h / Heating

With pyridine; 1H-imidazole; dmap; tributylphosphine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; ethanethiol; Tris(3,6-dioxaheptyl)amine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00080a014

Reference yield:

: 154698-94-9
(tert-Butyldiphenylsiloxy)methyl 2-<(methoxymethyl)oxy>-4-methylphenyl ketone

: 154699-07-7
(R)-(-)-2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-<(phenylthio)methyl>cyclobutanone

Guidance literature:: Multi-step reaction with 8 steps

1: 94 percent / NaH / tris<2-(2-methoxyethoxy)ethyl>amine / tetrahydrofuran / 62 °C / 1.) 10 h, 2.) 1 h

2: 91 percent / EtSH, BF₃*Et₂O / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) -23 deg C, 1.5 h

3: 99 percent / n-Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 1 h / Ambient temperature

4: 85 percent / pyridine / 2 h / Ambient temperature

5: 86 percent / imidazole, DMAP / dimethylformamide / 10 h / 0 °C

6: 100 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -23 °C

7: 96 percent / m-CPBA / CH₂Cl₂ / 0.25 h / Ambient temperature

8: 96 percent / tri-n-butylphosphine / tetrahydrofuran / 7 h / Heating

With pyridine; 1H-imidazole; dmap; tributylphosphine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; ethanethiol; Tris(3,6-dioxaheptyl)amine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00080a014