115351-18-3

Upstream product

• 37776-17-3 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose 
• 20398-90-7 6-azido-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 
• 100-39-0 benzyl bromide 

Downstream Products

• 128984-78-1 Trifluoro-methanesulfonic acid (3R,4S,5R)-5-((S)-2-amino-1-benzyloxy-ethyl)-4-benzyloxy-2-methoxy-tetrahydro-furan-3-yl ester 
• 121195-22-0 (1R,4S,5R,8R)-4,8-Bis-benzyloxy-7-methoxy-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester 
• 128984-81-6 N-benzyloxycarbonyl-2,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 121195-21-9 (1R,4S,5R,8R)-4,8-Bis-benzyloxy-7-methoxy-6-oxa-2-aza-bicyclo[3.2.1]octane 
• 19130-96-2 1,5-dideoxy-1,5-imino-D-glucitol 

Relevant academic research and scientific papers

Synthesis of nojirimycin derivatives

Nojirimycin δ-lactam and deoxynojirimycin are each synthesized from 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-L-idofuranose as a divergent intermediate by a method which comprises formation of the piperidine ring by connection of nitrogen between C-1 and C-5 with inversion of configuration at C-5 to form nojirimycin δ-lactam or between C-2 and C-6 with inversion of configuration at C-2.

SYNTHESIS OF DEOXYNOJIRIMYCIN AND OF NOJIRIMYCIN δ-LACTAM

The syntheses of nojirimycin δ-lactam and of deoxynojirimycin from a divergent ido-furanose intermediate are reported.

Synthesis of the antibiotic 1,5-dideoxy-1,5-imino-D-glucitol; concomitant formation of the D-mannitol analogue

The easy accessible 1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose was converted in six steps into 1,2-O-isopropylidene-3,6-di-O-benzyl-5-deoxy-5-azido-α-D-glucofuranose.The latter afforded, after acidolysis followed by hydrogenolysis, 1-deoxynojirimicine and a small quantity of 1-deoxymannonojirimicine.The antibiotic thus obtained had an inhibitory effect on the trimming of N-linked carbohydrates in IgM.