244092-54-4

Basic information

• Product Name: (R,E)-N-(4-methoxybenzylidene)-2-methylpropane-2-sulfinamide
• Synonyms: (R,E)-N-(4-methoxybenzylidene)-2-methylpropane-2-sulfinamide
• CAS NO: 244092-54-4
• Molecular Weight: 239.338
• Mol File: 244092-54-4.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (R,E)-N-(4-methoxybenzylidene)-2-methylpropane-2-sulfinamide(CAS DataBase Reference)
• NIST Chemistry Reference: (R,E)-N-(4-methoxybenzylidene)-2-methylpropane-2-sulfinamide(244092-54-4)
• EPA Substance Registry System: (R,E)-N-(4-methoxybenzylidene)-2-methylpropane-2-sulfinamide(244092-54-4)

Safety Data

• Hazardous Substances Data: 244092-54-4(Hazardous Substances Data)

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 159263-57-7 (R)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl tert-butanesulfinate 
• 196929-78-9 (R)-2-methylpropane-2-sulfinamide 

Downstream Products

• 865355-04-0 2-Methyl-propane-2-sulfinic acid [(1S,2R)-2-hydroxy-1-(4-methoxy-phenyl)-3-methyl-butyl]-amide 
• 870074-91-2 2-Methyl-propane-2-sulfinic acid [(1S,2R)-2-hydroxy-1-(4-methoxy-phenyl)-3-methyl-pentyl]-amide 
• 1029701-03-8 pinacol (R)-1-N-sulfinyl-4-methoxyphenyl-1-boronate 
• 1426585-73-0 C₁₈H₃₀BNO₄S 
• 1508278-77-0 C₃₀H₄₇NO₅SSi 
• 1429229-83-3 (R)-1-((R_S)-tert-butylsulfinyl)-2-(4-methoxyphenyl)-4-methylenepyrrolidine 
• 1429229-97-9 (S)-1-((R_S)-tert-butylsulfinyl)-2-(4-methoxyphenyl)-4-methylenepyrrolidine 
• 1333259-57-6 C₁₃H₁₉F₂NO₂S 
• 1298087-72-5 C₂₉H₄₂N₂O₆SSi 
• 1003317-76-7 ethyl (R)-3-((R)-1,1-dimethylethylsulfinamido)-2,2-difluoro-3-(4-methoxyphenyl)propanoate 

Relevant articles and documents

Design and Synthesis of TY-Phos and Application in Palladium-Catalyzed Enantioselective Fluoroarylation of gem-Difluoroalkenes

The first example of highly enantioselective fluoroarylation of gem-difluoroalkenes with aryl halides is presented by using a new chiral sulfinamide phosphine (Sadphos) type ligand TY-Phos. N-Me-TY-Phos can be easily synthesized on a gram scale from readily available starting materials in three steps. Salient features of this work including readily available starting materials, good yields, high enantioselectivities as well as broad substrate scope make this approach very practical and attractive. Notably, the asymmetric synthesis of an analogue of a biologically active molecule is also reported.

DMAP-Catalysed Sulfinylation of Diacetone- D -Glucose: Improved Method for the Synthesis of Enantiopure tert-Butyl Sulfoxides and tert-Butanesulfinamides

An improved method for the tert-butanesulfinylation of diacetone glucose with tert-butanesulfinyl chloride is reported. The method is based on a beneficial effect of catalytic DMAP, which enhances both the rate of the reaction and the enantioselectivity of the process to give (R S)-diastereomer 2 R S with a 94 % de and in quantitative yield. (R S)-DAG sulfinate ester 2 R S is an excellent intermediate for the synthesis of enantiopure tert-butyl sulfoxides. Grignard agents and organolithium reagents can displace smoothly the diacetone glucose moiety to give synthetically relevant enantiopure sulfoxides, including highly functionalized derivatives, in high yields and with high enantioselectivities. (R S)-DAG sulfinate ester 2 R S is also an excellent N-sulfinylating agent; simple addition of LiHMDS (lithium hexamethyldisilazide) in THF gives (S S)-tert-butanesulfinamide, and N-tert-butanesulfinylimines are then formed in a two-step one-pot manner. N-Alkylated tert-butanesulfinamides are formed by the condensation of 2 R S with lithium amides.

Design and characterization of mechanism-based inhibitors for the tyrosine aminomutase SgTAM

The synthesis and evaluation of two classes of inhibitors for SgTAM, a 4-methylideneimidazole-5-one (MIO) containing tyrosine aminomutase, are described. A mechanism-based strategy was used to design analogs that mimic the substrate or product of the reaction and form covalent interactions with the enzyme through the MIO prosthetic group. The analogs were characterized by measuring inhibition constants and X-ray crystallographic structural analysis of the co-complexes bound to the aminomutase, SgTAM.