109074-99-9

Upstream product

• 100-39-0 benzyl bromide 
• 109074-96-6 (2S, 3R, 4R, 5S)-1,2:5,6 diimino 3,4-O-methylethylidene hexane diol 
• 3969-59-3 mannitol triacetonide 
• 3969-84-4 3,4-di-O-isopropylidene-D-mannitol 
• 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 

Downstream Products

• 109075-00-5 1,2,5,6-tetradeoxy-1-methyl-2-(N-benzylamino)-3,4-O-(1-methylethylidene)-5,6-(N-benzylimino)-L-iditol 
• 109075-01-6 1,2,5,6-tetradeoxy-1-methyl-2,6-(N-benzylimino)-3,4-O-(1-methylethylidene)-5-(N-benzylamino)-L-iditol 
• 123074-12-4 1,2,5,6-tetradeoxy-1-(phenylthio)-2,6-(N-benzylimino)-3,4-O-(1-methylethylidene)-5-(N-benzylamino)-L-iditol 
• 114126-63-5 1,2,5,6-tetradeoxy-1-(phenylthio)-2-(N-benzylamino)-3,4-O-(1-methylethylidene)-5,6-(N-benzylimino)-L-iditol 
• 114126-66-8 1,2,5,6-tetradeoxy-1,6-bis(phenylthio)-2,5-bis(N-benzylamino)-3,4-O-(1-methylethylidene)-L-iditol 
• 114126-60-2 1,2,5,6-tetradeoxy-1-bromo-2,6-(N-benzylimino)-3,4-O-(1-methylethylidene)-5-(N-benzylamino)-L-iditol 

Relevant academic research and scientific papers

SYNTHESIS OF DIEPOXIDES AND DIAZIRIDINES, PRECURSORS OF ENANTIOMERICALLY PURE α-HYDROXY AND α-AMINO ALDEHYDES OR ACIDS, FROM D-MANNITOL

Specific activations or protections of the hydroxyl groups of 3-4-O-isopropylidene-D-mannitol 2 followed by intramolecular SN2 reactions, lead to the chiral diepoxides 4 and 7 and to the chiral diaziridines 9 and 13 precursors of enantiomerically pure α-hydroxy and α-amino aldehydes or 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.