S-ethyl (2S,3R)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate

Base Information

Chemical Name:S-ethyl (2S,3R)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate
CAS No.:138509-95-2
Molecular Formula:C₁₇H₂₈O₃SSi
Molecular Weight:340.559
Hs Code.:

Synonyms:S-ethyl (2S,3R)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of S-ethyl (2S,3R)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate

Chemical Property:

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Technology Process of S-ethyl (2S,3R)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate

There total 15 articles about S-ethyl (2S,3R)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate 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: 86.0%

: 100-52-7
benzaldehyde

: 138509-94-1
(Z)-1-(ethylthio)-1-(trimethylsiloxy)-2-(tert-butyldimethylsiloxy)ethene

: 138509-95-2
S-ethyl (2S,3R)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate

Guidance literature:: With tin(II) trifluoromethanesulfonate; chiral N-methyl-2-<(N'-isoindolinyl)methylene>pyrrolidine; dibutyltin diacetate; In dichloromethane; at -78 ℃; for 21h;
DOI:10.1021/ja00100a078

Reference yield:

: 100-52-7
benzaldehyde

: 138509-94-1
(Z)-1-(ethylthio)-1-(trimethylsiloxy)-2-(tert-butyldimethylsiloxy)ethene

: 138509-95-2
S-ethyl (2S,3R)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate

: (anti)-S-ethyl 2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate

Guidance literature:: With tin(II) trifluoromethanesulfonate; dibutyltin diacetate; (S)-1-methyl-2-[(dihydroisoindol-2-yl)methyl]pyrrolidine; In dichloromethane; at -78 ℃; for 21h; Yield given. Yields of byproduct given;
DOI:10.1002/chem.19970030914

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 138509-95-2
S-ethyl (2S,3R)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / imidazole / dimethylformamide / 10 h / Ambient temperature

2: 71 percent / aq. K₂CO₃ / methanol; tetrahydrofuran / 1 h / Ambient temperature

3: 100 percent / thionyl chloride / CH₂Cl₂ / 1.) reflux, 10 min, 2.) RT, 10 h

4: 78 percent / pyridine / CH₂Cl₂ / 10 h / Ambient temperature

5: 80 percent / LDA / tetrahydrofuran; hexane / -78 - 20 °C

6: tin(II) triflate, (S)-1-ethyl-2-<(1-piperidinyl)methyl>pyrrolidine, dibutyltin diacetate / CH₂Cl₂ / 20 h / -78 °C

With pyridine; 1H-imidazole; tin(II) trifluoromethanesulfonate; thionyl chloride; dibutyltin diacetate; (S)-1-Ethyl-2-<(piperidin-1-yl)methyl>pyrrolidine; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.67.1708