S-tert-butyl (3R)-3-hydroxy-3-phenylpropanethioate

Base Information

• Chemical Name: S-tert-butyl (3R)-3-hydroxy-3-phenylpropanethioate
• CAS No.: 112303-67-0
• Molecular Formula: C₁₃H₁₈O₂S
• Molecular Weight: 238.351
• Mol file: 112303-67-0.mol

Synonyms:S-tert-butyl (3R)-3-hydroxy-3-phenylpropanethioate

Chemical Property of S-tert-butyl (3R)-3-hydroxy-3-phenylpropanethioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of S-tert-butyl (3R)-3-hydroxy-3-phenylpropanethioate

There total 15 articles about S-tert-butyl (3R)-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: 71.0%

(1-tert-butylsulfanyl-vinyloxy)trimethylsilane (63584-47-4) + benzaldehyde (100-52-7) → S-tert-butyl (3R)-3-hydroxy-3-phenylpropanethioate (112303-67-0)

Guidance literature:

With phenol; titanium(IV) isopropylate; (R)-1,1'-Bi-2-naphthol; In diethyl ether; at 0 - 20 ℃;

DOI:10.1002/1099-0690(200210)2002:20<3419::AID-EJOC3419>3.0.CO;2-F

Reference yield:

(1-tert-butylsulfanyl-vinyloxy)trimethylsilane (63584-47-4) + benzaldehyde (100-52-7) → (S)-S-tert-butyl 3-hydroxy-5-phenylpropanethioate (104805-25-6) + S-tert-butyl (3R)-3-hydroxy-3-phenylpropanethioate (112303-67-0)

Guidance literature:

With tin(II) trifluoromethanesulfonate; tributyltin fluoride; (S)-1-methyl-2-<(piperidin-1-yl)-methyl>pyrrolidine; In dichloromethane; at -78 ℃; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/0022-328X(90)85213-I

Reference yield:

(1-tert-butylsulfanyl-vinyloxy)trimethylsilane (63584-47-4) → S-tert-butyl (3R)-3-hydroxy-3-phenylpropanethioate (112303-67-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / oxazaborolidinone / CH₂Cl₂ / 4 h / Ambient temperature

2: Bu₄NF / tetrahydrofuran / 0.5 h / Ambient temperature

3: 84 percent / PCC / CH₂Cl₂ / 5 h

4: Bn₂NH₂(CF₃CO₂) / benzene / 3 h

With oxazaborolidinone; tetrabutyl ammonium fluoride; pyridinium chlorochromate; dibenzylammonium trifluoroacetate salt; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1246/bcsj.69.3639

upstream raw materials:

S-tert-butyl thioacetate

benzaldehyde

1-ethylthio-1-(trimethylsiloxy)ethene

(1-tert-butylsulfanyl-vinyloxy)trimethylsilane

Refernces

• 1、 Zimmer, Reinhold,Peritz, Anke,Czerwonka, Regina,Schefzig, Luise,Reissig, Hans-Ulrich. "Optimisation, scope and limitations of enantioselective aldol reactions of an S-ketene silyl acetal with aliphatic aldehydes under (R)-BINOL-titanium(IV) catalysis conditions". . p. 3419 - 3428. Retrieved 2007/10/03.
• 2、 Gennari, Cesare,Vulpetti, Anna,Moresca, Daniela. "A Highly Enantio- and Diastereoselective Aldol Reaction for α-Heterosubstituted Thioacetates". . p. 4857 - 4860. Retrieved 2007/10/02.