132295-44-4

Usage

Uses

Used in Pharmaceutical Industry:
2,5-Anhydro-2,5-imino-D-glucitol is used as a therapeutic agent for the treatment of viral infections, cancer, diabetes, and obesity. The inhibition of glycohydrolases by 2,5-Anhydro-2,5-imino-D-glucitol could be of significant value in managing these conditions, as it interferes with the active sites of the enzymes and prevents their function.
Used in Research and Development:
In the field of research and development, 2,5-Anhydro-2,5-imino-D-glucitol serves as a valuable compound for studying the structure and function of glycohydrolases. Its potent inhibitory properties make it an essential tool in understanding the role of these enzymes in various biological processes and the development of new therapeutic strategies.
Used in Drug Design and Synthesis:
The unique chemical properties of 2,5-Anhydro-2,5-imino-D-glucitol make it a useful starting material for the design and synthesis of new drugs targeting glycohydrolases. Its ability to inhibit these enzymes can be leveraged to develop novel therapeutic agents for the treatment of various diseases, including viral infections, cancer, diabetes, and obesity.

InChI:InChI=1/C6H13NO4/c8-1-3-5(10)6(11)4(2-9)7-3/h3-11H,1-2H2/t3-,4+,5+,6?/m0/s1

Upstream product

• 135395-50-5 (2S,3R,4R)-2,5-Bis-hydroxymethyl-3,4-dihydro-2H-pyrrole-3,4-diol 
• 132803-73-7 5-azido-5-deoxy-L-sorbose 
• 912966-26-8 (2S,3R,4R,5R)-2,5-bis(hydroxymethyl)-1-tosylpyrrolidine-3,4-diol 
• 25018-67-1 1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose 
• 340969-90-6 5-azido-3,4-di-O-benzyl-5-deoxy-α-L-sorbopyranose 
• 136616-71-2 Phosphoric acid mono-((2R,3S,4R,5S)-5-azido-2,3,4-trihydroxy-tetrahydro-pyran-2-ylmethyl) ester 
• 156856-23-4 (2S,2'S)-<(1R,2R)-1,2-dibenzyloxy-ethan-diyl>bis(1-tert-butoxycarbonyl)-aziridine 
• 213457-86-4 (1R,4S,6S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxa-5-aza-bicyclo[2.2.1]heptan-3-one 
• 213457-99-9 (2R,3R,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-pyrrolidine-2-carboxylic acid methyl ester 
• 213457-88-6 Trifluoro-methanesulfonic acid (S)-1-[(2S,3R,4R)-4-amino-3-(tert-butyl-dimethyl-silanyloxy)-5-oxo-tetrahydro-furan-2-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester 
• 6347-01-9 fructopyranose 
• 1035406-36-0 ethyl 2,5-dideoxy-2,5-imino-L-gulonate 
• 1035405-82-3 2,5-dideoxy-2,5-imino-L-gulonic acid 
• 1097198-53-2 4-benzyloxy-1,3-ethylidenedioxy-2,5-dideoxy-2,5-imino-D-glucitol 

Downstream Products

• 191851-89-5 2,5-anhydro-N-benzyloxycarbonyl-2,5-imino-D-glucitol 
• 198076-36-7 (2S,3R,4R,5R)-2,5-Bis-hydroxymethyl-1-(3-nitro-benzyl)-pyrrolidine-3,4-diol 
• 162895-67-2 5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-formyl-N-methylpyrrolidine 
• 162895-66-1 5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)-N-methylpyrrolidine 
• 162895-79-6 N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine 
• 162895-80-9 N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-<<<(4-methylphenyl)sulfonyl>oxy>methyl>pyrrolidine 
• 162895-76-3 N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-<(2-amino-6-chloropurin-9-yl)methyl>pyrrolidine 
• 162895-77-4 N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(9-guaninylmethyl)pyrrolidine 
• 162992-53-2 5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine 
• 162992-52-1 8(R)-<(Benzyloxy)methyl>-6(R),7(R)-bis(benzyloxy)-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one 

Relevant academic research and scientific papers

2,5-Dideoxy-2,5-imino-D-mannitol and -D-glucitol. Two-step bio-organic syntheses from 5-azido-5-deoxy-D-glucofuranose and -L-idofuranose; evaluation as glucosidase inhibitors and application in affinity purification and characterisation of invertase from yeast

Glucose isomerase (EC 5.3.1.5) catalyzes the quantitative isomerisation of 5-azido-5-deoxy-D-gluco- (7) and -L-idofuranose (9), respectively, into the corresponding ketoses, 5-azido-5-deoxy-D-fructopyranose (8) and -L-sorbopyranose (10), respectively. Upon catalytic hydrogenation over palladium-on-charcoal, the fructose derivative 8 gives the natural product and the efficient glycosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol (4), while the sorbose derivative 10 affords 2,5-dideoxy-2,5-imino-D-glucitol (5). This represents a preparatively very simple and efficient two-step synthesis of these biologically active compounds. Both are strong inhibitors of α- and β-glucosidases from various sources, the D-manno-isomer 4 being distinctly more active. Because of its structural relationship with β-D-fructofuranose, compound 4 is also a vary good inhibitor of invertase from yeast and, as such, was for the first time employed, after immobilized and aminohexyl-sepharose, for the purification of this enzyme. Glucose isomerase (EC 5.3.1.5) catalyses the quantitative isomerization of 5-azido-5-deoxy-D-gluco (7) and -L-idofuranose (9), respectively, into the corresponding ketoses, 5-azido-5-deoxy-D-fructopyranose (8) and -L-sorbopyranose (10) respectively. Upon catalytic hydrogenation over palladium on 2,5-dideoxy-2,5-imino-D-mannitol (4), while the sorbose derivative 10 affords 2,5-dideoxy-2,5-imino-D-glucitol (5). This represents a preparatively very simple and efficient two-step synthesis of these biologically active compounds. Both are strong inhibitors of α- and β-glucosidases from various sources, the D-manno-isomer 4 being distinctly more active. Because of its structural relationship with β-D-fructofuranose, compound 4 is also a very good inhibitor of invertase from yeast and, as such, was for the first time employed, after immobilization on aminohexyl-sepharose, for the purification of this enzyme.

Potential intermediates for incorporation of polyhydroxylated prolines into combinatorial libraries

Bicyclic 2 and monocyclic 6 2-amino-1,4-lactones provide divergent intermediates for subsequent incorporation of polyhydroxylated prolines into combinatorial amide libraries. The X-ray crystal structure of an azidolactone, combined with molecular modellin

Asymmetric total syntheses of (+)-2,5-dideoxy-2,5-imino-D-glucitol [(+)-DGDP] and (?)-1-deoxymannojirimycin [(?)-DMJ] via an extended chiral 1,3-oxazine

The asymmetric total syntheses of (+)-2,5-dideoxy-2,5-imino-D-glucitol [(+)-DGDP] 1 and (?)-1-deoxymannojirimycin [(?)-DMJ] 2 were achieved using an extended chiral 1,3-oxazine. The key synthetic strategies included extension of the chirality of anti,syn-oxazine 3 using diastereoselective dihydroxylation, and piperidine and pyrrolidine ring formation. Starting from readily available anti,syn-oxazine 3, (+)-DGDP 1 was synthesized in 5 steps with 31.6% overall yield and (?)-DMJ 2 was synthesized in 4 steps with 60.6% overall yield.

Asymmetric syntheses of 2,5-dideoxy-2,5-imino-d-glucitol [(+)-DGDP] and 1,2,5-trideoxy-1-amino-2,5-imino-d-glucitol [(+)-ADGDP]

The asymmetric syntheses of 2,5-dideoxy-2,5-imino-d-glucitol [(+)-DGDP] and 1,2,5-trideoxy-1-amino-2,5-imino-d-glucitol [(+)-ADGDP] were achieved via the ring-closing iodoamination of an enantiopure bishomoallylic amine, followed by functionalisation of the resultant iodomethyl substituted pyrrolidine. In the case of (+)-DGDP, formation of the corresponding aziridinium ion followed by regioselective ring-opening with H2O gave the desired hydroxymethyl substituted pyrrolidine as a single diastereoisomer (>99:1 dr), with subsequent deprotection giving (+)-DGDP in good yield. Whereas in the case of (+)-ADGDP, displacement of iodide with NaN3 proved to be optimal, giving (+)-ADGDP in good yield after reduction and deprotection.

Synthesis of dihydroxymethyl dihydroxypyrrolidines and steviamine analogues from C-2 formyl glycals

Synthesis of dihydroxymethyl dihydroxypyrrolidines from C-2 formyl d-glycals has been described via a common dicarbonyl intermediate. The hence obtained pyrrolidines have been further utilized for the synthesis of some steviamine analogues. The newly synthesized molecules have been evaluated for glycosidase inhibition against 6 commercially available enzymes and found to be active in the micromolar range, where one of the steviamine analogues showed good and selective inhibition of β-mannosidase (Helix pomatia).

C-branched iminosugars: α-glucosidase inhibition by enantiomers of isoDMDP, isoDGDP, and isoDAB- l -isoDMDP compared to miglitol and miglustat

The Ho crossed aldol condensation provides access to a series of carbon branched iminosugars as exemplified by the synthesis of enantiomeric pairs of isoDMDP, isoDGDP, and isoDAB, allowing comparison of their biological activities with three linear isomeric natural products DMDP, DGDP, and DAB and their enantiomers. l-IsoDMDP [(2S,3S,4R)-2,4-bis(hydroxymethyl)pyrrolidine-3,4-diol], prepared in 11 steps in an overall yield of 45% from d-lyxonolactone, is a potent specific competitive inhibitor of gut disaccharidases [Ki 0.081 μM for rat intestinal maltase] and is more effective in the suppression of hyperglycaemia in a maltose loading test than miglitol, a drug presently used in the treatment of late onset diabetes. The partial rescue of the defective F508del-CFTR function in CF-KM4 cells by l-isoDMDP is compared with miglustat and isoLAB in an approach to the treatment of cystic fibrosis.

A convenient approach toward the synthesis of enantiopure isomers of DMDP and ADMDP

A practical method for the synthesis of five-membered iminocyclitols, pyrrolidine alkaloids bearing multiple hydroxyl substituents, has been developed. All of the eight key intermediates, enantiopure tri-O-benzyl cyclic nitrones, are prepared from four cheap, readily available d-aldopentoses. The nucleophilic addition of cyclic nitrones with vinyl magnesium chloride and TMSCN shows high 2,3-trans stereoselectivity. To construct the 2,3-cis configurations, inversion of the C-2 nitrile group is achieved via an elimination-reduction sequence. Using this approach, five isomers of DMDP and six isomers of ADMDP are prepared efficiently. In the biological evaluation, iminocyclitol 27 is a new and potent inhibitor against β-hexosaminidase with an IC50 value of 0.2 μM.

Synthesis of pyrrolidine homoazasugars and 3,4-dihydroxy-5- hydroxymethylprolines using aldol additions of metalated bislactim ethers to 2,4-O-ethylidene-d-erythroses

A strategy for the synthesis of 2,5-dideoxy-2,5-iminohexitols and 2,5-dideoxy-2,5-iminoglyconic acids is described by using diastereoselective aldol additions of metalated bislactim ethers to 2,4-O-ethylidene-d-erythroses and intramolecular N-alkylation a

Synthesis of (+)-DGDP and (-)-7-epialexine

The partial reduction of electron deficient pyrroles is an extremely versatile method that allows us to prepare substituted pyrrolidines and pyrrolizidines with trans-diol stereochemistry on the five membered ring. The 2008 Royal Society of Chemistry.

Regioselective intramolecular ring closure of 2-amino-6-bromo-2,6- dideoxyhexono-1,4-lactones to 5- or 6-membered iminuronic acid analogues: Synthesis of 1-deoxymannojirimycin and 2,5-dideoxy-2,5-imino-d-glucitol

1-Deoxymannojirimycin (8c) was synthesised from 2-amino-6-bromo-2,6- dideoxy-d-mannono-1,4-lactone (7) by intramolecular direct displacement of the C-6 bromine employing non-aqueous base treatment followed by reduction of the intermediate methyl ester. Li