54606-67-6

Upstream product

• 50-99-7 D-glucose 
• 76-83-5 trityl chloride 
• 100-44-7 benzyl chloride 
• 107-18-6 allyl alcohol 
• 209911-52-4 allyl 3-O-benzyl-D-glucopyranoside 
• 48149-74-2 allyl D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 100-39-0 benzyl bromide 
• 54631-72-0 (3R,4S,5S,6R)-2-allyloxy-6-(trityloxymethyl)tetrahydropyran-3,4,5-triol 
• 209911-56-8 2-propenyl 3-O-(phenylmethyl)-6-O-(triphenylmethyl)-D-glucopyranoside 

Downstream Products

• 2771-55-3 2,3,4-tri-O-benzyl-D-galactopyranoside 
• 88567-49-1 6-O-acetyl-2,3,4-tri-O-benzyl-α/β-D-galactopyranoside 
• 61277-56-3 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-α/β-D-galactopyranose 
• 157459-92-2 (R)-3-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-dodecanoic acid 
• 157459-93-3 (R)-3-((2R,3R,4S,5S,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-dodecanoic acid methyl ester 
• 157543-64-1 2,3,4-tri-O-benzyl-6-O-acetyl-α-D-galactopyranosyl chloride 
• 54606-68-7 ((2R,3R,4S,5R)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol 
• 1415306-06-7 2,3,4-tri-O-benzyl-1-O-tert-butyldiphenylsilyl-6-O-trityl-D-glucitol 
• 1415305-59-7 2,3,4-tri-O-benzyl-6-O-(dibenzylphosphatyl)-1-O-tert-butyldiphenylsilyl-5-O-propargyl-D-glucitol 
• 1415305-57-5 2,3,4-tri-O-benzyl-1-O-tert-butyldiphenylsilyl-5-O-propargyl-D-glucitol 
• 1415305-56-4 2,3,4-tri-O-benzyl-1-O-(dibenzylphosphatyl)-5-O-propargyl-6-O-trityl-D-glucitol 
• 1415305-55-3 2,3,4-tri-O-benzyl-5-O-propargyl-6-O-trityl-D-glucitol 
• 1415305-54-2 2,3,4-tri-O-benzyl-1-O-tert-butyldiphenylsilyl-5-O-propargyl-6-O-trityl-D-glucitol 
• 120048-16-0 2,3,4-tri-O-benzyl-6-O-trityl-α-D-glucopyranose 

Relevant academic research and scientific papers

DIOXA-BICYCLO[3.2.1.]OCTANE-2,3,4-TRIOL DERIVATIVES

Compounds of Formula (I) are described herein and the uses thereof for the treatment of diseases, conditions and/or disorders mediated by sodium-glucose transporter inhibitors (in particular, SGLT2 inhibitors).The compounds disclosed herein are useful for the prevention and treatment of obesity and its associated co-morbidities, inn particular type Il (type 2) diabetes.

A practical synthetic method for α- and β-glycosyloxyacetic acids

Dihydroxylation of allyl 2,3,4-tri-O-benzyl-6-O-tritylglycosides provides diols, the anomers of which can easily be separated by column chromatography in a practical scale. These anomers can be cleanly transformed into α- and β-glycosyloxyacetic acids, respectively, via oxidative cleavage of the diol followed by oxidation.

A synthetic route from D-glucose to D-myo-inositol-1,4,5- tris(dihydrogenphosphate): Use of an unusual ene reaction and the Bu2SnCl2/Bu2SnH2 reagent

D-Glucose was converted into the propargylsilane aldehyde 3, which underwent ring closure with retention of silicon, in the presence of camphorsulfonic acid, to give 5, and this was elaborated, via ketone 22, into 2, which had previously been transformed into D-myo-inositol-1,4,5- tris(dihydrogenphosphate). A crucial step in the synthesis is the stereoselective reduction of 22 with Bu2SnCl2/Bu2SnH2, a reagent system that shows a strong preference for generating equatorial alcohols.