20746-71-8

Usage

Chemical Structure

Contains a sugar molecule (glucopyranoside derivative)

Functional Groups

Allyl and benzyl groups

Properties

Antimicrobial: Due to the presence of allyl and benzyl groups
Antifungal: Also attributed to allyl and benzyl groups

Applications

Pharmaceutical: Studied for potential use in drug development
Medical: Investigated for potential treatments for various diseases

Ongoing Research

Continues to be studied for specific properties and medical applications

Upstream product

• 100-39-0 benzyl bromide 
• 20746-64-9 allyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 48149-72-0 (2S,3R,4S,5R,6R)-2-Allyloxy-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 1056479-53-8 allyl-4,6-O-benzylidene-2,3-di-O-hydroxy-D-mannopyranoside 
• 100-44-7 benzyl chloride 
• 530-26-7 D-Mannose 
• 182212-07-3 α,β-O-allyl-D-mannopyranoside 
• 618-31-5 benzylidene dibromide 
• 119111-33-0 (3aS,5aR,8R,9aR,9bS)-4-Allyloxy-2,8-diphenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxine 
• 214490-84-3 Allyl 2,3,4,6-Tetra-O-acetyl-D-mannopyranoside 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 

Downstream Products

• 61893-74-1 allyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside 
• 72333-20-1 allyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 
• 129437-65-6 allyl O-(3,4,6-tri-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 
• 1369405-80-0 (3R,4R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-5,5-difluorotetrahydro-2H-pyran-2-one 

Relevant academic research and scientific papers

5,5-Difluoro- and 5-Fluoro-5-methyl-hexose-based C-Glucosides as potent and orally bioavailable SGLT1 and SGLT2 dual inhibitors

(2S,3R,4R,5S,6R)-2-Aryl-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diols and (2S,3R,4R,5S,6R)-2-aryl-5-fluoro-5-methyl-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diols were discovered as dual inhibitors of sodium glucose co-transporter proteins (

5,5-DIFLUORO- AND 5-FLUORO-5-METHYL-C-GLYCOSIDE DERIVATIVES USEFUL AS DUAL SGLT1 / SGLT2 MODULATORS

The present invention is directed to 5,5-difluoro- and 5-fluoro-5-methyl-C-glycoside derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT activity, more particularly dual SGLT1/2 activity.

BENZOCYCLOBUTANE DERIVATIVES USEFUL AS DUAL SGLT1/SGLT2 MODULATORS

The present invention is directed to benzocyclobutane derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT activity, more particularly dual SGLT1/2 activity. More particularly, the compounds of the present invention are useful in the treatment of for example, Type II diabetes mellitus, Syndrome X, and complications and symptoms associated with said disorders.

Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols

A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely α-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by 3JC,H coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective.

1,3,4,6-Tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranose as a glycosyl donor in syntheses of oligosaccharides

1,3,4,6-Tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranose was tested as a glycosyl donor for oligosaccharide synthesis via ferric chloride-catalyzed coupling reaction.Glycosyl acceptors tried (6 in all) were O-benzyl-protected D-galactosides having free OH groups at positions 3 and 4, respectively, and similarly protected glycosides of D-glucose and 2-acetamido-2-deoxy-D-glucose unsubstituted on O-4.Existing syntheses of all the acceptors were improved, in four instances by exploitation of Garegg and Hultberg's cyanoborohydride procedure for the conversion 4,6-O-benzylidene -> 6-O-benzyl .Good to excellent yields of β-linked disaccharides were obtained from the galactoside and glucoside acceptors, but with allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside, stereoselectivity was lost (α:β-ratio 1:2).Allyl and benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosides gave, respectively, the allyl and benzyl β-glycosides of the donor as major products.A mechanism is proposed for this transglycosidation reaction.The N-chloroacetyl groups in the disaccharide products were readily converted into N-acetyl by reduction with zinc-acetic acid.

Stereochemical Control in Hex-5-enyl Radical Cyclizations: From Carbohydrates to Carbocycles. 3

The hex-5-enyl radical cyclization reaction was applied to prepare highly oxygenated cyclopentanoids from aldopyranose sugars.The Wittig reaction of the sugars readily provides hex-5-en-1-ols which were converted to hex-5-enyl radicals via one of the vari