16958-26-2

Upstream product

• 69465-27-6 5-azido-5-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 
• 100-39-0 benzyl bromide 
• 18006-23-0 3,6-Di-O-benzyl-1,2-O-isopropylidene-β-L-ido-furanose 
• 115351-17-2 Trifluoro-methanesulfonic acid (S)-2-benzyloxy-1-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester 

Downstream Products

• 127708-83-2 5-Azido-3,6-di-O-benzyl-5-deoxy-α/β-D-glucofuranose 
• 115369-07-8 C₂₀H₂₃N₃O₅ 
• 115351-20-7 C₂₀H₂₃N₃O₅ 
• 128984-74-7 5-Amino-5-deoxy-3,6-di-O-benzyl-D-glucono-δ-lactam 
• 128984-73-6 5-azido-3,6-di-O-benzyl-5-deoxy-D-glucono-1,4-lactone 
• 14904-83-7 nojirimycin-δ-lactam 
• 127656-54-6 (E/Z)-2,3,4,6-tetra-O-benzyl-5-deoxy-5-trifluoroacetamido-D-glucose oxime 
• 127656-46-6 (E/Z)-5-Azido-2,3,4,6-tetra-O-benzyl-5-deoxy-D-glucose oxime 
• 127656-38-6 (E/Z)-5-Azido-3,6-di-O-benzyl-5-deoxy-D-glucose methoxime 
• 127656-34-2 (E/Z)-5-Azido-3,6-di-O-benzyl-5-deoxy-D-glucose oxime 
• 127656-55-7 2,3,4,6-Tetra-O-benzyl-5-deoxy-5-trifluoroacetamido-D-glucononitrile 
• 127656-53-5 2,3,4,6-Tetra-O-benzyl-5-deoxy-5-trifluoroacetamido-D-glucose 
• 127656-52-4 2,3,4,6-Tetra-O-benzyl-5-deoxy-5-trifluoroacetamido-D-glucitol 
• 127656-45-5 5-Azido-2,3,4,6-tetra-O-benzyl-5-deoxy-D-glucose 

Relevant academic research and scientific papers

Looking glass inhibitors: scalable syntheses of DNJ, DMDP, and (3R)-3-hydroxy-l-bulgecinine from d-glucuronolactone and of l-DNJ, l-DMDP, and (3S)-3-hydroxy-d-bulgecinine from l-glucuronolactone. DMDP inhibits β-glucosidases and β-galactosidases whereas l-DMDP is a potent and specific inhibitor of α-glucosidases

A convenient large-scale synthesis of 1-deoxynojirimyin (DNJ) from d-glucuronolactone involves introduction of azide at C-5 with retention of configuration to give 5-azido-5-deoxy-1,2-O-isopropylidene-α-d-glucofuranose as a key intermediate in an overall yield of up to 72%; the same intermediate can be transformed into DMDP [(2R,3R,4R,5R)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol] and (3R)-3-hydroxy-l-bulgecinine [(2S,3R,4R,5R)-3,4-dihydroxy-5-hydroxymethyl-l-proline]. l-Glucuronolactone, a readily available l-sugar chiron, may similarly be used to access the enantiomers l-DNJ, l-DMDP, and (3S)-3-hydroxy-d-bulgecinine. A comparison of glycosidase inhibition by DMDP (an inhibitor of β-glucosidases and β-galactosidases) and l-DMDP (a potent and specific α-glucosidase inhibitor) with the corresponding enantiomeric hydroxybulgecinines is reported; DMDP and (3R)-3-hydroxy-l-bulgecinine show weak inhibition of glycogen phosphorylase.

Synthesis of (1-13C)-1-deoxynojirimycin

(1-13C)-1-Deoxynojirimycin was synthesised from easily available 5- azido-5-deoxy-1,2-O-isopropylidene-α-D-glucofuranose via a one-carbon chain shortening/chain extension sequence employing 13C-enriched potassium cyanide.

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.