109075-02-7

Upstream product

• 109074-96-6 (2S, 3R, 4R, 5S)-1,2:5,6 diimino 3,4-O-methylethylidene hexane diol 
• 52948-44-4 1,6-diazido-1,6-dideoxy-3,4-O-methylethylidene-D-mannitol 
• 53754-41-9 1,6-di-O-(p-toluenesulfonyl)-3,4-O-isopropylidene-D-mannitol 
• 109075-06-1 (S)-2-((4R,5R)-2,2-dimethyl-5-((S)-1-tosylaziridin-2-yl)-1,3-dioxolan-4-yl)-1-tosyl-aziridine 

Downstream Products

• 109075-03-8 1,2,5,6-tetradeoxy-1,6-dimethyl-2,5-bis-L-iditol 
• 93380-05-3 methyl 2(S)-butanoate 

Relevant academic research and scientific papers

Nucleophilic Opening of Chiral Bis(aziridines): A Route to Enantiomerically Pure α-Amino Aldehydes or Acids and Polysubstituted Piperidines

α-Amino aldehydes or acids can be obtained by nucleophilic opening of suitably protected chiral bis(aziridines) derived from D-mannitol.Nucleophiles consist of a wide range of organometallic and heteronucleophilic reagents.Reaction orientation toward bis-

NUCLEOPHILIC OPENING OF CHIRAL BIS-AZIRIDINES: A ROUTE TO ENANTIOMERICALLY PURE α-AMINO ACIDS AND POLYSUBSTITUTED PIPERIDINES

Suitably protected chiral functionalised bis-aziridines, prepared from D-mannitol, are opened by various organometallic reagents ( organomagnesium, -lithium and -copper derivatives ) as well as by heteronucleophiles (N3(1-), Br(1-), Cl(1-), HS(1-), PhS(1-)).Orientation of the reaction toward diopening (route to enantiomerically pure α-amino acids) or toward heterocyclisation (route to chiral, polysubstituted piperidines) is influenced, notably, by the nature of the N-protecting group and of the nucleophile and by the presence or not of Lewis acids.

DIASTEREOSPECIFIC SYNTHESIS OF DIAZIRIDINES FROM D-MANNITOL. ACCESS TO CHIRAL α-AMINOACIDS.

Nucleophilic opening of chiral diastereoisomeric diaziridines obtained from D-mannitol leads to precursors of D or L α-aminoacids (or aldehydes) and also provides a means of synthesizing polyhydroxylated piperidines.