(-)-(S_S)-(toluene-4-sulfinyl)-acetic acid tert-butyl ester

Base Information

• Chemical Name: (-)-(S_S)-(toluene-4-sulfinyl)-acetic acid tert-butyl ester
• CAS No.: 94404-20-3
• Molecular Formula: C₁₃H₁₈O₃S
• Molecular Weight: 254.35
• Mol file: 94404-20-3.mol

Synonyms:(-)-(S_S)-(toluene-4-sulfinyl)-acetic acid tert-butyl ester

Chemical Property of (-)-(S_S)-(toluene-4-sulfinyl)-acetic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(S_S)-(toluene-4-sulfinyl)-acetic acid tert-butyl ester

There total 5 articles about (-)-(S_S)-(toluene-4-sulfinyl)-acetic acid tert-butyl 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: 96.0%

acetic acid tert-butyl ester (540-88-5) + (1S,2R,5S)-2-isopropyl-5-methylcyclohexyl (R)-4-methylbenzenesulfinate (1517-82-4,13064-80-7,20752-45-8,50444-99-0,83060-18-8,83060-21-3,91796-57-5,98147-48-9,124819-73-4,132829-99-3,134929-63-8,91177-13-8) → (-)-(SS)-(toluene-4-sulfinyl)-acetic acid tert-butyl ester (94404-20-3)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 - -35 ℃; for 3h;

DOI:10.1016/j.tetlet.2008.02.033

Reference yield: 70.0%

acetic acid tert-butyl ester (540-88-5) + (-)-menthyl p-toluenesulfinate (1517-82-4) → (-)-(SS)-(toluene-4-sulfinyl)-acetic acid tert-butyl ester (94404-20-3)

Guidance literature:

With diisopropylamine; In tetrahydrofuran; diethyl ether; at -40 ℃; for 18h;

DOI:10.1002/hlca.19970800104

Reference yield:

tert-butyl 1-(p-tolylthio)acetate (36304-27-5) → tert-butyl (R)-p-toluenesulfinylacetate (58059-08-8) + (-)-(SS)-(toluene-4-sulfinyl)-acetic acid tert-butyl ester (94404-20-3)

Guidance literature:

With benzenesulfonamide; sodium periodate; borate buffer solution; at 20 ℃; for 4h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; pH 9;

DOI:10.1021/jo00206a008

upstream raw materials:

tert-butyl 1-(p-tolylthio)acetate

acetic acid tert-butyl ester

4-Methyl-benzenesulfinic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester

(-)-menthyl p-toluenesulfinate

Downstream raw materials:

C₂₃H₃₀O₅S

C₂₃H₃₀O₅S

(1R,2R,αR,Rs)-(+)-(5,5-dimethyl-2-isopropenyl)-α-p-toluenesulfinylhexaneacetate

1,1-dimethylethyl (3S)-3-hydroxy-5-(phenylmethoxy)pentanoate

Refernces

• 1、 Bauder, Claude. "Diastereofacial selectivity in aldol-type condensation induced by optically pure α-sulfinyl acetate with α-substituted aldehydes". . p. 2243 - 2246. Retrieved 2008/09/19.
• 2、 Itoh,Matsuyama,Yoshida,Kamigata,Iyoda. "Asymmetric synthesis of 4-phenyl-1,5-diazacyclooctan-2-one using optically active vinyl sulfoxides". . p. 3121 - 3130. Retrieved 2007/10/03.