67734-35-4

Usage

Uses

Used in Organic Synthesis:
(R)-tert-Butanethiosulfinate is used as a reagent in organic synthesis for the preparation of chiral sulfoxides, which are important building blocks in the creation of various pharmaceuticals and agrochemicals.
Used in Flavoring and Aroma Compounds:
Leveraging its characteristic odor reminiscent of garlic or onion, (R)-tert-Butanethiosulfinate is used as a flavoring and aroma compound in food products, enhancing the sensory experience of various culinary creations.
Used in Pharmaceutical Development:
(R)-tert-Butanethiosulfinate is studied for its potential antimicrobial and antifungal properties, making it a subject of interest for the development of new pharmaceutical products aimed at treating infections and diseases.
Used in Agricultural Product Development:
(R)-tert-Butanethiosulfinate's antimicrobial and antifungal properties are also being explored for use in agricultural products, potentially contributing to the development of new pesticides or fungicides to protect crops and enhance agricultural yields.

InChI:InChI=1/C8H18OS2/c1-7(2,3)10-11(9)8(4,5)6/h1-6H3/t11-/m1/s1

Upstream product

• 110-06-5 di-tert-butyl disulfide 

Downstream Products

• 220263-59-2 (R_S)-2-methyl-N-(1-phenylethylidene)propane-2-sulfinamide 
• 1192110-12-5 bis(2-((R)-tert-butylsulfinyl)phenoxy)methane 
• 4170-71-2 (R)-(tert-butylsulfinyl)benzene 
• 1192110-03-4 1-(R)-(+)-tert-butylsulfinyl-2-methoxybenzene 
• 1192110-02-3 1-(R)-(+)-tert-butylsulfinyl-2-methylbenzene 
• 1192110-04-5 1-(R)-(+)-tert-butylsulfinyl-2-(methoxymethoxy)benzene 
• 1192110-14-7 1-((R)-tert-butylsulfinyl)-2-(3-(2-((R)-tert-butylsulfinyl)phenoxy)propoxy)benzene 
• 1192110-13-6 1,2-bis(2-((R)-tert-butylsulfinyl)phenoxy)ethane 
• 1220531-60-1 (R,R)-1,2-bis(tert-butylsulfinyl)benzene 
• 1191465-70-9 (R(S))-(-)-1-(tert-butylsulfinyl)-3-methoxybenzene 
• 1310329-93-1 C₁₂H₁₈O₃S 
• 1310329-82-8 (R)-(2-(tert-butylsulfinyl) phenyl) (methyl) sulfane 
• 1310329-94-2 C₁₂H₁₈O₃S 
• 1310329-80-6 (R)-(2-(tert-butylsulfinyl)phenyl) (phenyl) sulfane 

Relevant academic research and scientific papers

Process for synthesizing chiral tert-butanesulfinyl amide

The invention discloses a process for synthesizing chiral tert-butanesulfinyl amide. The process includes carrying out reaction on tert-butyl mercaptan and iodine/hydrogen peroxide acetone to generate di-tert-butyl disulfide; oxidizing hydrogen peroxide under the catalytic effect of vanadium to generate chiral tert-butyl sulfenyl tert-butyl mercaptide; carrying out one-pot reaction on the chiral tert-butyl sulfenyl tert-butyl mercaptide and lithium reagents/liquid ammonia in the presence of alkyl chloride to obtain the tert-butanesulfinyl amide. Compared with existing processes, the process has the advantages that the smoothness of the process can be enhanced, the usage of the liquid ammonia can be reduced to a great extent, and the operational efficiency can be improved.

NEW PROCESSES AND INTERMEDIATES USEFUL IN SYNTHESIS OF NEP INHIBITORS

The invention relates to a novel process, novel process steps and novel intermediates useful in the synthesis of pharmaceutically active compounds, in particular neutral endopeptidase (NEP) inhibitors such as sacubitril, and prodrugs thereof.

Enantioselective organocatalytic oxidation of functionalized sterically hindered disulfides

Figure presented The first study on enantioselective oxidation of functionalized sterically hindered disulfides is reported. This study shows that the Shi organocatalytic system using carbohydrate-derived ketone with oxone is superior to the Ellman-Bolm v

Catalytic enantioselective oxidation of sulfides and disulfides by a chiral complex of bis-hydroxamic acid and molybdenum

A chiral bis-hydroxamic acid (BHA)-molybdenum complex was used for the catalytic asymmetric oxidation of sulfides and disulfides utilizing one equivalent of alkyl peroxide with yields up to 83% and ee up to 86%. An extension of our methodology combines the asymmetric oxidation with kinetic resolution providing excellent enantioselectivity (ee 92-99%).

Contra-Friedel-Crafts tert-butylation of substituted aromatic rings via directed metallation and sulfinylation

Directed metallation and sulfinylation yields sulfoxides which undergo ipso nucleophilic aromatic substitution with tertiary and secondary alkyllithiums, giving aromatic rings bearing alkyl groups generally incompatible with directed metallation methods and with regioselectivity complementary with classical Friedel-Crafts substitution. The Royal Society of Chemistry 2006.

Enantioselective synthesis of thiosulfinates and of acyclic alkylidenemethylene sulfide sulfoxides

Enantioselectivities up to 75 % have been found in the catalytic mono-oxidation of di-tert-butyl disulfide and related compounds as well as of ketene-S,S-acetals with an in situ generated chiral dioxirane. The effect of solvents on the enantiomeric excess

An Economic Approach to Chiral Thiosulfinates by Enantioselective Oxidation with Hydroperoxide

Some novel chiral ligands and VO(acac)2 were utilized to catalytic asymmetric oxidation of disulfides. The optically active thiosulfinates were obtained.

Improved synthesis of tert-butanesulfinamide suitable for large-scale production

(Matrix presented) An improved synthesis of tert-butanesulfinamide that overcomes the scalability problems of the previous syntheses is described. The key step is the catalytic asymmetric oxidation of the inexpensive di-tert-butyl disulfide starting material. The new homogeneous reaction conditions utilize an inexpensive chiral ligand prepared in a single step from commercially available cis-1-amino-indan-2-ol. The reaction is performed at a 2.3 M concentration in the practical solvent acetone and can readily be run on a kilogram scale.

Enantioselective oxidation of di-tert-butyl disulfide with a vanadium catalyst: Progress toward mechanism elucidation

The mechanism of the oxidation of di-tert-butyl disulfide (1) to the chiral thiosulfinate (2) by H2O2 catalyzed by bis(acetylacetonato)oxovanadium and a chiral Schiff-base ligand (3) has been investigated. Techniques included 51V NMR spectroscopy, solvent effects on reaction enantioselectivity, and the isolation and full characterization of a 2:1 ligand-to-vanadium catalyst precursor. A model for the dramatic solvent effect on the enantioselectivity of this reaction was developed, based on the identification of a competing nonselective oxidation pathway. From this model, strategies for limiting this competing pathway were developed.