Benzenepropanethioic acid, b-hydroxy-, S-(1,1-dimethylethyl) ester, (S)-

Base Information

• Chemical Name: Benzenepropanethioic acid, b-hydroxy-, S-(1,1-dimethylethyl) ester, (S)-
• CAS No.: 104805-25-6
• Molecular Formula: C13H18O2S
• Molecular Weight: 238.351
• Mol file: 104805-25-6.mol

Synonyms:

Chemical Property of Benzenepropanethioic acid, b-hydroxy-, S-(1,1-dimethylethyl) ester, (S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzenepropanethioic acid, b-hydroxy-, S-(1,1-dimethylethyl) ester, (S)-

There total 11 articles about Benzenepropanethioic acid, b-hydroxy-, S-(1,1-dimethylethyl) ester, (S)- 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: 90.0%

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

Guidance literature:

With titanium(IV) isopropylate; 4 A molecular sieve; (S)-[1,1']-binaphthalenyl-2,2'-diol; In diethyl ether; at -20 ℃; for 12h;

DOI:10.1021/ja00113a031

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)-S-tert-butyl 3-hydroxy-5-phenylpropanethioate (104805-25-6)

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:

Ketene

benzaldehyde

stannous 2-methyl-2-propanethiolate

S-tert-butyl thioacetate

Refernces

• 1、 Keck, Gary E.,Krishnamurthy, Dhileepkumar. "Pronounced solvent and concentration effects in an enantioselective mukaiyama aldol condensation using BINOL-titanium(IV) catalysts". . p. 2363 - 2364. Retrieved 1995.
• 2、 Kinugasa, Motoharu,Hanada, Toshiro,Egusa, Takayuki,Fujita, Katsuhiro,Oku, Akira. "Asymmetric Synthesis of Functionalized Secondary Alcohols by Catalytic Ring-Cleavage Reactions of Cyclic Acetals Derived from (R)-1,3-Butanediol". . p. 3639 - 3650. Retrieved 2007/10/03.