192317-17-2

Upstream product

• 192317-15-0 Methanesulfonic acid (S)-((4S,5R)-5-benzylcarbamoyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester 
• 100-46-9 benzylamine 
• 192317-13-8 N-benzyl-2,3:5,6-di-O-isopropylidene-D-gulonamide 
• 67642-42-6 2,3,5,6-di-O-isopropylidene-D-gulono-1,4-lactone 

Downstream Products

• 192317-31-0 (3aR,6R,6aR)-5-Benzyl-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-thione 

Relevant academic research and scientific papers

Sugar lactams and lactim ethers, useful precursors of cyclic amidines, from intramolecular nucleophilic displacements

The cyclisation of the conjugate base of N-aryl-2,3:5,6-di-O-isopropylidene-4-O-methanesulfonyl-D- gulonamides gave the D-allonolactam acetals. Sodium methoxide-promoted cyclisation of 2,3:5,6-di-O-isopropylidene-4-O-methanesulfonyl-D-mannononitrile gave the D-talonolactim ether. Tetrazole formation without isolation of the intermediate azide was illustrated by the conversion of the aforementioned nitrile sulfonate into the D-talonotetrazole. Cyclic amidines were prepared from the lactam and lactim ether derivatives. The D-allono derivatives were also converted into D-ribono-1,4 lactam and amidine derivatives.