130780-94-8

Upstream product

• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 80312-69-2 N-t-butoxycarbonyl-D,L-serinamide 
• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 
• 22821-76-7 4-(methylsulfonyl)benzonitrile 
• 33898-53-2 2-cyanoaziridine 

Downstream Products

• 130780-93-7 O³-Tosyl-L-serinnitril 
• 130780-93-7 rac-Serinnitril-hydrotosylat 

Relevant academic research and scientific papers

Decarboxylative Cyanation of Aliphatic Carboxylic Acids via Visible-Light Flavin Photocatalysis

An operationally simple method is disclosed for the decarboxylative cyanation of aliphatic carboxylic acids at room temperature. Riboflavin tetraacetate, which is an inexpensive organic photocatalyst, promotes the oxidation of carboxylic acids upon visible-light activation. After decarboxylation, the generated radicals are trapped by TsCN, yielding the desired nitriles without any further additive, in a redox-neutral process. Importantly, this protocol can be adapted to flow conditions.

Chemistry of α-Aminonitriles. Aziridin-2-carbonitrile, a Source of Racemic O3-Phosphonoserinenitrile and Glycolaldehyde Phosphate

Racemic aziridine-2-carbonitrile (rac-1) in MeCN solution reacts regioselectively (>90percent) with 2 equiv. of TsOH at room temperature to form the hydrotosylate of racemic O3-tosylserinenitrile (rac-2) via a β-ring opening (Scheme 2).A similar regioselective reaction takes place between rac-1 and H3PO4 to produce racemic O3-phosphoserinenitrile (rac-3) which is in turn a source of glycolaldehyde phosphate (=formylmethyl dihydrogenphosphate) under the conditions of a 'retro-Strecker' reaction in aqueous solution (Scheme 6).These experiments document a close structural relationship between the simplest of the sugar phosphates and an α-aminonitrile precursor.

Chemistry of alpha-aminonitriles. Aziridine-2-carbonitrile: photochemical formation from 2-aminopropenenitrile

2-Aminopropenenitrile in solvents such as MeCN, MeOH, or H2O is photoisomerized by UV light to racemic aziridine-2-carbonitrile (rac-2); the larger part of the starting material, however, fragments to HCN and MeCN. The observed photocyclization constitutes a structural connection within an ensemble of C3H4N2 compounds considered to be potentially relevant to prebiotic chemistry.