35023-63-3

Upstream product

• 90-05-1 2-methoxy-phenol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 2280-44-6 D-Glucose 
• 83-87-4 D-glucose pentaacetate 

Downstream Products

• 6092-24-6 2-methoxybenzoyl-β-D-glucopyranoside 
• 163852-97-9 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(5-bromo-2-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

Synthesis and structural characterization of new benzylidene glycosides, cytotoxicity against cancer cell lines and molecular modeling studies

This work describes the synthesis, structural characterization (by combined Fourier Transform Infrared - FTIR, 1H and 13C Nuclear Magnetic Resonance - NMR spectroscopy and High Resolution Mass Spectrometry - HRMS) and biological evaluation of a new series of glycosides designed from a benzylidene glucoside derived from eugenol (23) active against Candida glabrata. The mass accuracy between the calculated and found values observed in HRMS analyses were lower than 5 ppm, which are acceptable for proposing a molecular formula using this technique. We decided to keep the benzylidene group of 23, while changing either the saccharide unit (glucose or galactose) or the natural aglycone (eugenol, isoeugenol, dihydroeugenol or guaiacol) to check their influence in antifungal activity. Since the chemical modifications performed did not contribute to enhance the antifungal activity, the synthesized compounds (23–30) were further screened against four cancer cell lines (HeLa: cervix carcinoma; MDA-MB-231: breast carcinoma; T-24: urinary bladder carcinoma; and TOV-21G: ovarian carcinoma). The glucoside 27 showed promising activities (IC50 10.08–59.91 μM) against all the assayed cancer cell lines and higher values of selectivity index than doxorubicin, the control drug. The galactoside 28 demonstrated interesting results against HeLa, MDA-MB-231 and T-24 cells. This compound was active at 17.41 μM with a selectivity index greater than 13.7 against the HeLa cells, while doxorubicin was active at 10.01 μM with a selectivity index close to 1.5 considering this cell line. Further, we performed docking studies of these compounds with type II topoisomerase-DNA complex (TOP2) in order to try to explain their mechanism of action.

Stereoselectivity of reactions at the glycoside center of carbohydrates: VII. Synthesis of aryl α- and -β-D-glucopyranosides by Helferich, catalyzed by boron trifluoride etherate

13C NMR spectroscopy was used to study the stereoselectivity of glycosylation of phenols with the α and β anomers of penta-O-acetyl-D-glucopyranose, penta-O-trifluoroacetyl-D-glucopyranose, and 2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-D-glucopyranose in the presence of boron trifluoride etherate at varied temperature, time, and catalyst amount. The boron trifluoride etherate-catalyzed reaction of penta-O-acetyl-β -D-glucopyranose and 2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-β -D-glucopyranose with phenols occurs with a high stereocontrol to give, depending on conditions, predominantly 1,2-cis- or 1,2-trans-aryl-glycosides. This reaction can be used for preparative synthesis of the α- and β-anomeric forms of glycosides of a wide range of phenols.

Glycosides. Part 1. New Synthesis of 1,2-trans O-Aryl Glycosides, via Tributyltin Phenoxides

A new method of glycosidation of phenols has been studied.The reaction of tributyltin phenoxides 2 with 1,2,3,4,6-penta-O-acetyl-D-hexopyranosides 3, 7 and 9, in the presence of tin tetrachloride is described.Glycosides 4, 8 and 10 have been isolated in g

Synthesis and Antiinflammatory Activity of Some Glycosidated 3-Methylpyrazolin-5-(4H)-one-4-benzylidenes

The substituted hydroxybenzaldehyde 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosides (IIA-H), obtained by the stereospecific synthesis using phase transfer catalysis, on condensation with 3-methylpyrazolin-5-(4H)-one in the presence of piperidine yield the title compounds (IIIA-H).The effect of various phase transfer catalysts has been studied during the preparation of II.Compounds III have been tested for their antiinflammatory activity.