98260-66-3

Upstream product

• 131053-25-3 methyl 3-O-benzyl-2,6-imino-2,5,6-trideoxy-D-lyxo-hexofuranoside 
• 501-53-1 benzyl chloroformate 
• 113000-79-6 methyl N-benzyloxycarbonyl-3-O-benzyl-2,6-dideoxy-2,6-imino-5-O-phenyloxythiocarbonyl-α-D-mannofuranoside 
• 98260-67-4 methyl N-benzyloxycarbonyl-3-O-benzyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside 
• 16895-86-6 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose-5,6-carbonate 
• 16895-87-7 methyl-3-O-benzyl-α-D-glucofuranoside-5,6-carbonate 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 98260-64-1 methyl 2-azido-3-O-benzyl-2-deoxy-α-D-mannofuranoside 
• 98260-63-0 methyl 2-azido-3-O-benzyl-2-deoxy-α-D-mannofuranoside-5,6-carbonate 
• 98260-62-9 methyl 3-O-benzyl-2-O-trifluoromethanesulphonyl-α-D-glucofuranoside-5,6-carbonate 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 131053-27-5 3-O-benzyl-N-benzyloxycarbonyl-2,6-imino-2,5,6-trideoxy-D-lyxo-hexono-1,4-lactone 
• 53185-12-9 D-fagomine 
• 131053-26-4 (2S,3R,4R)-3-Benzyloxy-2-formyl-4-hydroxy-piperidine-1-carboxylic acid benzyl ester 
• 98260-69-6 4-O-benzyl-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-arabino-hexitol 

Relevant academic research and scientific papers

Synthesis of homochiral β-hydroxy-α-aminoacids [2S,3R,4R)-3, 4-dihydroxyproline and (2S,3R,4R)-3,4-dihydroxypipecolic acid] and of 1,4-dideoxy-1,4-imino-D-arabinitol [DAB1] and fagomine [1,5-imino-1,2,5-trideoxy-D-arabino-hexitol]

Efficient syntheses from diacetone glucose of 1,4-dideoxy-1, 4-imino-D-arabinitol, (2S,3R,4R)-3,4-dihydroxyproline, fagomine [1,5-imino-1,2,5-trideoxy-D arabino-hexitol], and (2S,3R,4R)-3,4)-3,4-dihydroxpipecolic acid by intramolecular nucleophilic displacement by an amino function of 2-O-trifluoromethanesulphonates of anomeric mixtures of methyl furanosides are reported.

SYNTHESIS OF DEOXYMANNOJIRIMYCIN FAGOMINE DEOXYNOJIRIMYCIN 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-MANNITOL 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-GLUCITOL 2S,3R,4R,5R-TRIHYDROXYPIPECOLIC ACID AND 2S,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID FROM METHYL 3-O-BENZYL-2,6-DIDEOXY-2,6-IMINO-α-D-...

The value of methyl 3-O-benzyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside as a divergent intermediate for the preparation of polyhydroxylated piperidines is illustrated by the synthesis of deoxymannojirimycin (1,5-dideoxy-1,5-imino-D-mannitol), fagomine (1,5-imino-1,2,5-trideoxy-D-arabino-hexitol), deoxynojirimycin (1,5-dideoxy-1,5-imino-D-glucitol), 2-acetamido-1,5-imino-1,2,5-trideoxy-D-mannitol, 2-acetamido-1,5-imino-1,2,5-trideoxy-D-glucitol, 2S,3R,4R,5R-trihydroxypipecolic acid and 2S,3R,4R,5S-trihydroxypipecolic acid.