96333-59-4

Usage

Chemical Properties

Off-White Solid

Upstream product

• 88607-79-8 (E)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one 
• 100-39-0 benzyl bromide 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 23243-67-6 3-(4-benzyloxyphenyl)-1-(2,4-dibenzyloxy-6-hydroxyphenyl)prop-2-en-1-one 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 480-41-1 naringenin 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 

Downstream Products

• 480-10-4 astragalin 
• 1254190-95-8 4',7-di-O-benzyl-3-O-(2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)kaempferol 
• 1254190-96-9 4',7-di-O-benzyl-3-O-(2-O-(α-L-rhamnopyranosyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)kaempferol 
• 30652-27-8 4',7-di-O-benzyl-kaempferol 
• 97828-25-6 5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-8-iodo-4H-chromen-4-one 
• 41440-05-5 isoscutellarein 
• 527-95-7 herbacetin 
• 32375-14-7 7-(benzyloxy)-2-(4-(benzyloxy)phenyl)-5-hydroxy-4H-chromen-4-one 
• 849938-27-8 5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)-3-[3,4-di-O-acetyl-2-O-benzyl-α-L-rhamnopyranosyloxy]-4H-chromen-4-one 
• 133882-73-2 Kaempferol-3-O-(2,4-di-O-acetyl-alpha-L-rhamnopyranoside) 
• 77307-50-7 Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside) 
• 135618-17-6 Kaempferol-3-O-(4-O-acetyl-alpha-L-rhamnopyranoside) 
• 482-39-3 kaempferol 3-rhamnoside 
• 916069-08-4 (2S,3S,4S,5R,6S)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3- yl)oxy)-5-hydroxy-2-methyltetrahydro-2H-pyran-3,4-diyl diacetate 

Relevant academic research and scientific papers

Synthesis of Benzopyran-Fused Flavone Derivatives via Microwave-Assisted Intramolecular C-H Activation

A microwave-assisted intramolecular direct arylation method for the synthesis of benzopyran-fused flavone derivatives containing natural flavone backbones is described. Different polyalkoxy flavones were synthesized and functionalized with 2-bromobenzyl bromide. The resulting compounds were subjected to palladium-catalyzed intramolecular direct arylation reactions supported by microwave irradiation to produce fused tetracyclic flavones. In the case of the 7-substituted chrysin derivative, the regioselectivity of the coupling was also examined.

Facile synthesis of norwogonin, isoscutellarein, and herbacetin

An expeditious synthesis of norwogonin, isoscutellarein, and herbacetin, has been accomplished by a strategy featuring a borylation of sterically hindered aryl iodide and a one-pot oxidation to generate the C-3 and C-8 OH groups. The total synthesis gives excellent yields and conventional flash column chromatography is not needed for purification.

Size and branching effects on the fluorescence of benzylic dendrimers possessing one apigenin fluorophore at the core

Different generations of dendrimers incorporating one fluorescent core of apigenin and three Fréchet benzylic dendrons have been prepared. The chief geometric features of these dendrimers have been obtained by Molecular Dynamics simulations. These computa

Study of kaempferol glycoside as an insulin mimic reveals glycon to be the key active structure

Diabetes mellitus is increasing in prevalence with patient numbers rising throughout the world. Current treatments for diabetes mellitus focus on control of blood glucose levels. Certain kinds of flavonoids or their glycosides stimulate cells to improve glucose uptake and lower blood glucose levels. We synthesized kaempferol 3-O-neohesperidoside (1), a naturally occurring substance present in Cyathea phalerata Mart., reported to mimic the action of insulin. Synthetic 1 promoted glucose uptake in the cultured cell line, L6. Further studies to determine the core structure responsible for this activity using synthetic compounds revealed neohesperidose to be the primary pharmacophore. These findings support the use of certain saccharides as a potential novel treatment for diabetes mellitus by replacing or supporting insulin.

De novo asymmetric syntheses of SL0101 and its analogues via a palladium-catalyzed glycosylation

(Chemical Equation Presented) The enantioselective syntheses of naturally occurring kaempferol glycoside SL0101 (1a) and its analogues 1b-e, as well as their enantiomers, have been achieved in 7-10 steps. The routes rely upon a diastereoselective palladium-catalyzed glycosylation, ketone reduction, and dihydroxylation to introduce the rhamno-stereochemistry. The asymmetry of the sugar moiety of these kaempferol glycosides was derived from Noyori reduction of an acylfuran. An acetyl group shift from an axial (C-2) to equatorial position (C-3) under basic conditions was also described.

Synthesis of a potent and selective inhibitor of p90 Rsk

(Chemical Equation Presented) The synthesis of the naturally occurring kaempferol glycoside SL0101 has been accomplished, as has its biochemical evaluation. SL0101 exhibits selective and potent p90 Rsk inhibitory activity at nanomolar concentrations without inhibiting the function of upstream kinases such as MEK, Raf, or PKC. The synthesis verified the structural assignment of the natural product and has provided access to material sufficient for detailed biological evaluation.