thiocarbonic acid [(1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-2,2-dimethyl-4-(2-methoxymethoxyethyl)cyclobutyl] ester p-tolyl ester

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Chemical Name:thiocarbonic acid [(1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-2,2-dimethyl-4-(2-methoxymethoxyethyl)cyclobutyl] ester p-tolyl ester
CAS No.:952101-31-4
Molecular Formula:C₂₄H₄₀O₅SSi
Molecular Weight:468.73
Hs Code.:

Synonyms:thiocarbonic acid [(1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-2,2-dimethyl-4-(2-methoxymethoxyethyl)cyclobutyl] ester p-tolyl ester

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Chemical Property of thiocarbonic acid [(1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-2,2-dimethyl-4-(2-methoxymethoxyethyl)cyclobutyl] ester p-tolyl ester

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Technology Process of thiocarbonic acid [(1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-2,2-dimethyl-4-(2-methoxymethoxyethyl)cyclobutyl] ester p-tolyl ester

There total 6 articles about thiocarbonic acid [(1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-2,2-dimethyl-4-(2-methoxymethoxyethyl)cyclobutyl] ester p-tolyl ester 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%

: 952101-30-3
(1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-2,2-dimethyl-4-(2-methoxymethoxyethyl)cyclobutan-3-ol

: 937-63-3
p-Tolyl chlorothionoformate

: 952101-31-4
thiocarbonic acid [(1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-2,2-dimethyl-4-(2-methoxymethoxyethyl)cyclobutyl] ester p-tolyl ester

Guidance literature:: With pyridine; dmap; In dichloromethane; for 16h;
DOI:10.1021/jo070861r

Reference yield:

: (4R,5R)-4-benzyloxy-2-methoxy-3,3-dimethyl-5-vinyltetrahydrofuran

: 952101-31-4
thiocarbonic acid [(1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-2,2-dimethyl-4-(2-methoxymethoxyethyl)cyclobutyl] ester p-tolyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 74 percent / BF₃*OEt₂; n-butyllithium / Cp₂ZrCl₂ / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 °C

3.1: BH₃*THF / tetrahydrofuran / 4 h / 0 - 20 °C

3.2: 94 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 4 h / 0 - 20 °C

4.1: 100 percent / ethyldiisopropylamine; tetrabutylammonium iodide / CH₂Cl₂ / 48 h

5.1: 100 percent / hydrogen / Pd/C / tetrahydrofuran / 24 h / 31029.7 Torr

6.1: 89 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h

With pyridine; 2,6-dimethylpyridine; dmap; n-butyllithium; borane-THF; boron trifluoride diethyl etherate; hydrogen; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; zirconocene dichloride; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo070861r

Reference yield:

: 895532-66-8
(1S,3S,4R)-3-benzyloxy-2,2-dimethyl-4-vinylcyclobutanol

: 952101-31-4
thiocarbonic acid [(1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-2,2-dimethyl-4-(2-methoxymethoxyethyl)cyclobutyl] ester p-tolyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 °C

2.1: BH₃*THF / tetrahydrofuran / 4 h / 0 - 20 °C

2.2: 94 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 4 h / 0 - 20 °C

3.1: 100 percent / ethyldiisopropylamine; tetrabutylammonium iodide / CH₂Cl₂ / 48 h

4.1: 100 percent / hydrogen / Pd/C / tetrahydrofuran / 24 h / 31029.7 Torr

5.1: 89 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h

With pyridine; 2,6-dimethylpyridine; dmap; borane-THF; hydrogen; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo070861r