95189-02-9

Usage

Type of compound

Synthetic chemical compound

Potential applications

Medicinal and pharmaceutical

Function

Potent and selective inhibitor of glucosidase enzymes

Enzyme target

Glucosidase enzymes involved in the breakdown of complex carbohydrates

Effect on blood sugar levels

Reduction in blood sugar levels

Potential treatment for

Diabetes

Additional therapeutic potential

Treatment of lysosomal storage disorders

Mechanism of action in lysosomal storage disorders

Reduction of harmful substance accumulation within cells

Current status

Ongoing research into potential therapeutic uses and derivatives

InChI:InChI=1/C6H13NO4/c8-2-4(10)5-6(11)3(9)1-7-5/h3-11H,1-2H2/t3-,4+,5-,6-/m1/s1

Upstream product

• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 22169-72-8 3-azido-3-deoxy-6-O-toluene-p-sulphonyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 114894-82-5 benzyl 6-O-tetra-butyldiphenylsilyl-α-D-mannopyranoside 
• 128442-44-4 Methanesulfonic acid (R)-((4R,5R)-5-azidomethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester 
• 128442-45-5 1-azido-1-deoxy-2,3-O-isopropylidene-4-O-methanesulphonyl-D-mannitol 
• 128442-43-3 4,5-anhydro-1-azido-1-deoxy-2,3-O-isopropylidene-D-talitol 
• 7115-24-4 (R)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]((4R,5R)-2,2-dimethyl-5-{[(methylsulfonyl)oxy]methyl}-1,3-dioxolan-4-yl)methyl methanesulfonate 
• 98362-01-7 [(4R,5R)-5-((2S,3R)-3-Hydroxymethyl-oxiranyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-carbamic acid benzyl ester 
• 95066-29-8 benzyl 4-amino-4-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside 
• 91652-76-5 1-benzyl 4-azido-4-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside 
• 114894-72-3 3,6-dideoxy-3,6-imino-1,2-O-isopropylidene-α-D-glucofuranose p-toluenesulphonate 
• 100806-48-2 (1R,5S,6R,1'S)-7-tert-butoxycarbonyl-6-1',2'-dihydroxyethyl-3,3-dimethyl-2,4-dioxa-7-azabicyclo<3.3.0>octane 
• 95066-30-1 1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-mannitol 
• 55951-90-1 1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose 

Relevant academic research and scientific papers

Epimerization of C5 of an: N -hydroxypyrrolidine in the synthesis of swainsonine related iminosugars

Epimerization of C5 of an N-hydroxypyrrolidine ring by regioselective oxidation to a nitrone followed by diastereoselective reduction provides a new approach to the synthesis of swainsonine and related compounds. The only protection in the synthesis of the potent mannosidase inhibitor DIM (1,4-dideoxy-1,4-imino-d-mannitol) was the acetonation of d-mannose.

SYNTHESIS OF THE MANNOSIDASE INHIBITORS SWAINSONINE AND 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL AND OF THE RING CONTRACTED SWAINSONINES, (1S, 2R, 7R, 7aR)-1,2,7-TRIHYDROXYPYRROLIZIDINE AND (1S, 2R, 7S, 7aR)-1,2,7-TRIHYDROXYPYRROLIZIDINE.

4,5-Anhydro-1-azido-1-deoxy-2,3-O-isopropylidene-D-talitol is a divergent intermediate for the efficient and practical syntheses of 1,4-dideoxy-1,4-imino-D-mannitol, swainsonine and of the ring contracted swainsonines, (1S, 2R, 7R, 7aR)-1,2,7-trihydroxypyrrolizidine and (1S, 2R, 7S, 7aR)-1,2,7-trihydroxypyrrolizidine.The effect on glycosidases of the ring contracted swainsonines is reported.

3,6-DIDEOXY-3,6-IMINO-1,2-O-ISODROPYLIDENE-α-D-GLUCOFURANOSE AS A DIVERGENT INTERMEDIATE FOR THE SYNTHESIS OF HYDROXYLATED PYRROLIDONES: SYNTHESIS IF 1,4-DIDEOXY-1,4-IMINO-L-GULITOL, 1,4-DIDEOXY-1,4-IMINO-D-LYXITOL, 2S,3S,4R,-3,4-DIHYDROXYPROLINE AND (1S,

An efficient synthesis of the p-toluenesulphonate salt of 3,6-dideoxy-3,6-imino-1,2-O-isopropylidene-α-D-glucofuranose (1) from glucose is reported; the potential of (1) in making hydroxylated pyrrolidines is illustrated by the preparation of 1,4-dideoxy-

SYNTHESIS OF THE α-MANNOSIDASE INHIBITORS SWAINSONINE AND 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL FROM MANNOSE

4-azido-4-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside is a key intermediate in the syntheses of the α-mannosidase inhibitors, swainsonine and 1,4-dideoxy-1,4-imino-D-mannitol, and of the α-galactosidase inhibitor 1,4-dideoxy-1,4-imino-D-lyxitol, from mannose.

Design Synthesis and Preliminary Evaluation of a Potent &α-Mannosidase Inhibitor: 1,4-Dideoxy-1,4-imino-D-mannitol

1,4-Dideoxy-1,4-imino-D-mannitol (1), synthesised from benzyl α-D-mannopyranoside, is a potent competitive inhibitor of the hydrolysis of p-nitrophenyl α-D-mannopyranoside catalysed by Jack Bean α-mannosidase (Canavalia ensiformis); this is the first repo