135910-13-3

Upstream product

• 609-06-3 L-xylose 
• 13039-67-3 (2S,3S,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol 
• 41546-31-0 L-xylose 
• 137820-47-4 (3R,4R,5S)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene 
• 169736-18-9 (2S,3R,4S)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5-methoxyoxolane 
• 16838-89-4 2,3,5-tri-O-benzyl-L-xylofuranose 

Downstream Products

• 1129725-82-1 (2S,3R,4R)-1-benzyl-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]piperidine 
• 922163-68-6 2,3,5-tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(1-trityl-1H-imidazol-2-yl)-pentan-1-ol 
• 922163-70-0 benzoic acid 2,3,5-tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-diiodo-1H-imidazol-2-yl)-pentyl ester 
• 922163-75-5 6,7-bis-benzyloxy-5-benzyloxymethyl-8-(tert-butyl-dimethyl-silanyloxy)-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine 
• 922163-71-1 Benzoic acid (1R,2R,3R,4S)-2,3,5-tris-benzyloxy-1-(4,5-diiodo-1H-imidazol-2-yl)-4-hydroxy-pentyl ester 
• 922163-69-7 benzoic acid 2,3,5-tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(1H-imidazol-2-yl)-pentyl ester 
• 922163-73-3 6,7-bis-benzyloxy-5-benzyloxymethyl-8-(tert-butyl-dimethyl-silanyloxy)-2,3-diiodo-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine 
• 922163-78-8 N-(6,7-bis-benzyloxy-5-benzyloxymethyl-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-8-yl)-isobutyramide 
• 922163-72-2 Benzoic acid (5R,6R,7S,8R)-6,7-bis-benzyloxy-5-benzyloxymethyl-2,3-diiodo-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-8-yl ester 
• 922163-77-7 (5R,6R,7R,8S)-8-Azido-6,7-bis-benzyloxy-5-benzyloxymethyl-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine 
• 922163-74-4 6,7-bis-benzyloxy-5-benzyloxymethyl-8-(tert-butyl-dimethyl-silanyloxy)-2-iodo-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine 
• 922163-76-6 (5R,6R,7R,8R)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-8-ol 
• 922499-10-3 (2R,3S,4S)-2,3,5-Tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-pentan-1-ol 
• 922163-66-4 (2S,3S,4S)-2,3,5-Tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-pentanal 

Relevant academic research and scientific papers

Oxidation of N,N-Disubstituted Hydroxylamines to Nitrones with Hypervalent Iodine Reagents

Hypervalent iodine compounds are viable reagents for the oxidation of N,N-disubstituted hydroxylamines to the corresponding nitrones, with IBX performing best. The procedure is very simple and user-friendly and affords the target compounds with high effic

Synthesis of d -Fagomine and Its Seven- and Eight-Membered Higher-Ring Analogues, and the Formal Synthesis of (+)-Australine from l -Xylose-Derived Chiron

The synthesis of d-fagomine and its seven- and eight-membered higher-ring analogues from commercially available l-xylose is reported. The syntheses involve elaboration of a common alkenol precursor obtained from l-xylose-derived hemiacetal. The key steps

Synthesis and Evaluation of Hybrid Structures Composed of Two Glucosylceramide Synthase Inhibitors

Glucosylceramide metabolism and the enzymes involved have attracted significant interest in medicinal chemistry, because aberrations in the levels of glycolipids that are derived from glucosylceramide are causative in a range of human diseases including lysosomal storage disorders, type2 diabetes, and neurodegenerative diseases. Selective modulation of one of the glycoprocessing enzymes involved in glucosylceramide metabolism - glucosylceramide synthase (GCS), acid glucosylceramidase (GBA1), or neutral glucosylceramidase (GBA2) - is therefore an attractive research objective. In this study we took two established GCS inhibitors, one based on deoxynojirimycin and the other a ceramide analogue, and merged characteristic features to obtain hybrid compounds. The resulting 39-compound library does not contain new GCS inhibitors; however, a potent (200nm) GBA1 inhibitor was identified that has little activity toward GBA2 and might therefore serve as a lead for further biomedical development as a selective GBA1 modulator. Taking the best of both: Two established glucosylceramide synthase (GCS) inhibitors were merged via convergent synthesis to obtain hybrid compounds. Members of this 39-compound library have characteristics of both parent GCS inhibitors. No new GCS inhibitors were established, but a potent (200nm) acid glucosylceramidase (GBA1) inhibitor was identified. This adamantanemethyloxypenanoic acid pyrrolidene-substituted derivative of eliglustat can serve as a lead for further biomedical development of selective GBA1 modulators.

SELECTIVE GLYCOSIDASE INHIBITORS

The present invention provides glucoimidazole derivatives and methods of making them. The compounds can be used to inhibit the activity of O-GlcNAcase enzymes, including both bacterial OGA (bOGA) and human OGA (hOGA) and can be selective, showing low inhi

GLYCOSIDASE INHIBITORS AND METHODS OF SYNTHESIZING SAME

The compounds of the present invention relate to chain-extended and chain-modified analogues of salacinol, including embodiments where the sulfate moiety has been substituted with a carboxylate or phosphate moiety. In other embodiments the sulfate moiety has been shifted by one carbon atom in the zwitterionic structure. In another embodiment the polyhydroxylated side chain may be replaced with a lipophilic alkyl chain and a suitable counterion. The invention also encompasses methods for synthesizing the salacinol analogues and using the analogues for enzyme inhibition applications.

GlcNAcstatin: A picomolar, selective O-GlcNAcase inhibitor that modulates intracellular O-GlcNAcylation levels

Many phosphorylation signal transduction pathways in the eukaryotic cell are modulated by posttranslational modification of specific serines/threonines with N-acetylglucosamine (O-GlcNAc). Levels of O-GlcNAc on key proteins regulate biological processes a

α-glucosidase inhibitors

This invention relates to novel N-glycosyl derivatives of 1,4-dideoxy-1,4-imino-D-arabinitol, to the chemical processes for their preparation, to their α-glucosidase inhibiting properties, and to their end-use application in the treatment of diabetes, obe