10396-97-1

Basic information

• Product Name: Benzenesulfonamide, 4-methyl-N-(tetrahydro-2-oxo-3-furanyl)-, (S)-
• Synonyms: N-p-toluenesulfonyl-L-homoserine lactone;(S)-N-tosylhomoserine γ-lactone;N-tosylhomoserine lactone;4-methyl-N-((S)-2-oxotetrahydrofuran-3-yl)benzenesulfonamide;4-Methyl-N-((S)-2-oxo-tetrahydro-furan-3-yl)-benzenesulfonamide;L-N-tosyl-α-amino-γ-butyrolactone
• CAS NO: 10396-97-1
• Molecular Formula: C11H13NO4S
• Molecular Weight: 255.295
• Mol File: 10396-97-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 136-138 °C
• Boiling Point: 471.6±55.0 °C(Predicted)
• Density: 1.38±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Benzenesulfonamide, 4-methyl-N-(tetrahydro-2-oxo-3-furanyl)-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, 4-methyl-N-(tetrahydro-2-oxo-3-furanyl)-, (S)-(10396-97-1)
• EPA Substance Registry System: Benzenesulfonamide, 4-methyl-N-(tetrahydro-2-oxo-3-furanyl)-, (S)-(10396-97-1)

Safety Data

• Hazardous Substances Data: 10396-97-1(Hazardous Substances Data)

Upstream product

• 143947-81-3 [(S)-5-Oxo-3-(toluene-4-sulfonyl)-oxazolidin-4-yl]-acetaldehyde 
• 6305-38-0 (S)-(-)-α-amino-γ-butyrolactone hydrobromide 
• 98-59-9 p-toluenesulfonyl chloride 
• 88613-49-4 (S)-3-[(4-methylphenyl)sulfonyl]-5-oxo-4-oxazolidineacetic acid 
• 4816-82-4 N-[(4-methylphenyl)-sulfonyl]-L-aspartic acid 

Downstream Products

• 1056879-43-6 N-[(1S,2S)-2-hydroxy-1-(2-hydroxyethyl)but-3-enyl]-4-methylbenzenesulfonamide 

Relevant articles and documents

A novel and convenient route to L-homoserine lactones and L-phosphinothricin from L-aspartic acid

An efficient synthesis of L-phosphinothricin and N-protected-L-homoserine lactone derivatives starting from L-aspartic acid is described.

A microwave-assisted synthesis of (S)-N-protected homoserine γ-lactones from l-aspartic acid

A three-pot preparation of (S)-N-protected homoserine γ-lactones is presented. Conversion of N-protected l-aspartic acid to an oxazolidinone is followed by selective reduction/acid-catalyzed cyclization to deliver the lactones. Microwave irradiation proved valuable for improving the latter reaction steps in some cases.

A general, iterative, and modular approach toward carbohydrate libraries based on ruthenium-catalyzed oxidative cyclizations

(Chemical Equation Presented) Carbohydrates are an omnipresent class of highly oxygenated natural products. Due to their wide spectra of biological activities, they have been in the center of synthetic organic chemistry for more than 130 years. During the past 50 years non-natural carbohydrates attracted the interest of various chemists in the fields of organic, biological, and medical chemistry. Especially desoxygenated sugars proved to be an important class of compounds. Up to date, most non-natural analogues are synthesized starting from natural, enantiomerically pure carbohydrates in multistep synthesis. In this report, we present a synthetic strategy that allows the selective modular synthesis of natural and non-natural carbohydrates within five synthetic steps starting from readily available starting materials. Due to a sequential introduction of O-or N-functionalities, a regioselective protection of each new functional group is possible. The key step in the carbohydrate synthesis is a RuO4-catalyzed oxidative eyclization via a pH-dependent dehydrogenation-dihydroxylation-cyclization or an oxidative fragmentation-cyclization, leading to highly substituted new carbohydrates, in which each functional group is orthogonally protected and accessible for further synthetic operations.