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

Base Information

• Chemical Name: S-ethyl (2R,3R)-2-(t-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate
• CAS No.: 138509-96-3
• Molecular Formula: C₁₇H₂₈O₃SSi
• Molecular Weight: 340.559
• Mol file: 138509-96-3.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about S-ethyl (2R,3R)-2-(t-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:

benzaldehyde (100-52-7) + (Z)-1-(ethylthio)-1-(trimethylsiloxy)-2-(tert-butyldimethylsiloxy)ethene (138509-94-1) → S-ethyl (2S,3R)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate (138509-95-2) + S-ethyl (2R,3R)-2-(t-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate (138509-96-3) + S-ethyl (2R,3S)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate (159573-36-1)

Guidance literature:

With tin(II) trifluoromethanesulfonate; dibutyltin diacetate; (S)-1-Ethyl-2-<(piperidin-1-yl)methyl>pyrrolidine; In dichloromethane; at -78 ℃; for 20h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1246/bcsj.67.1708

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → S-ethyl (2R,3R)-2-(t-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate (138509-96-3)

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

Reference yield:

ethyl 2-(tert-butyldimethylsilyloxy)acetate (67226-78-2) → S-ethyl (2R,3R)-2-(t-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate (138509-96-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) trimethylaluminum / 1.) hexane, a) -78 deg C, b) 0 deg C, 1 h, 2.) CH₂Cl₂, hexane, RT, 1 h

2: 80 percent / LDA / tetrahydrofuran; hexane / -78 - 20 °C

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

With tin(II) trifluoromethanesulfonate; dibutyltin diacetate; trimethylaluminum; (S)-1-Ethyl-2-<(piperidin-1-yl)methyl>pyrrolidine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1246/bcsj.67.1708

upstream raw materials:

benzaldehyde

(Z)-1-(ethylthio)-1-(trimethylsiloxy)-2-(tert-butyldimethylsiloxy)ethene

ethyl 2-(tert-butyldimethylsilyloxy)acetate

(tert-butyldimethylsiloxy) acetic acid tert-butyldimethylsilyl ester