10396-97-1

Upstream product

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

Relevant academic research and scientific papers

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 general strategy for the synthesis of enantiomerically pure azetidines and aziridines through nickel-catalyzed cross-coupling

Abstract In this communication, we report a straightforward synthesis of enantiomerically pure 2-alkyl azetidines. The protocol is based on a highly regioselective nickel-catalyzed cross-coupling of aliphatic organozinc reagents with an aziridine that fea

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.

Stereocontrolled total syntheses of isodomoic acids G and H via a unified strategy

Marine neuroexcitatory compounds isodomoic acids G and H were efficiently synthesized from a common intermediate using a silicon-based cross-coupling reaction. Dividing each target compound into the core fragment and the side-chain fragment enabled the synthesis to be convergent. The trans-2,3-disubstituted pyrrolidine core fragment was accessed through a diastereoselective rhodium-catalyzed carbonylative silylcarbocyclization reaction of a vinylglycine-derived 1,6-enyne. A stereochemically divergent desilylative iodination reaction was developed to convert the cyclization product to both E- and Z-alkenyl iodides, which would eventually lead to isodomoic acid G and isodomoic acid H, respectively. The late-stage alkenyl-alkenyl silicon-based cross-coupling reaction uniting the core alkenyl iodides and the side-chain alkenylsilanol was achieved under mild conditions. Finally, two mild deprotections afforded the target molecules.

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.

Stereocontrolled synthesis of substituted N-arenesulfonyl azetidines from γ-(phenylseleno)alkyl arylsulfonamides

Different synthetic methodologies for the stereocontrolled synthesis of substituted azetidines are reported. The approach utilizes an optimized oxidation reaction of γ-(phenylseleno)alkyl arylsulfonamides, followed by the intramolecular substitution of th