20398-90-7

Upstream product

• 4648-54-8 trimethylsilylazide 
• 37776-17-3 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose 
• 100-39-0 benzyl bromide 
• 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 
• 23313-03-3 (R)-2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl 4-methylbenzenesulfonate 
• 23313-05-5 6-azido-3-O-benzyl-6-deoxy-1,2-O-(1-methylethylidene)-α-D-glucofuranose 

Downstream Products

• 115351-18-3 1,2-O-isopropylidene-3,5-di-O-benzyl-6-azido-6-deoxy-β-L-idofuranose 
• 82231-16-1 benzyl 6-azido-2,3,4-tri-O-benzyl-6-deoxy-β-L-idopyranose 
• 1354048-93-3 (2R)-2-[(3aR,5S,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-7-(4-tert-butylphenyl)-5-phenyl-2,3-dihydro-1,4-oxazepine 
• 1354048-91-1 (2R)-2-[(3aR,5S,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-5-(3-fluorophenyl)-7-phenyl-2,3-dihydro-1,4-oxazepine 
• 1354048-92-2 (2R)-2-[(3aR,5S,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-7-(3-methylphenyl)-5-(2-thienyl)-2,3-dihydro-1,4-oxazepine 
• 1354048-94-4 (2R)-2-[(3aR,5S,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-7-(4-tert-butylphenyl)-5-(4-ethylphenyl)-2,3-dihydro-1,4-oxazepine 
• 1354048-90-0 (2R)-2-[(3aR,5S,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-7-phenyl-5-(2-thienyl)-2,3-dihydro-1,4-oxazepine 
• 1354048-96-6 (2R)-2-[(3aR,5S,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-7-(4-methoxyphenyl)-5-(2-thienyl)-2,3-dihydro-1,4-oxazepine 
• 1354048-89-7 (2R)-2-[(3aR,5S,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-5-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1,4-oxazepine 
• 1354048-88-6 (2R)-2-[(3aR,5S,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-5,7-diphenyl-2,3-dihydro-1,4-oxazepine 
• 1354048-95-5 (2R)-2-[(3aR,5S,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-7-(4-methoxyphenyl)-5-phenyl-2,3-dihydro-1,4-oxazepine 
• 1354048-97-7 (2R)-2-[(3aR,5S,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-7-phenyl-5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-1,4-oxazepine 
• 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 

Relevant academic research and scientific papers

The Synthesis of L-aminosugar and the studies of L-pyranoses on the ring III of pyranmycins.

The synthesis of a novel class of aminoglycoside, pyranmycin, and a convenient method for the preparation of 6-amino-L-idopyranosides were reported. One of the members in the reported pyranmycin families, TC010, has prominent activity against Escherichia

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 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.