35023-63-3

Basic information

• Product Name: 2-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• Synonyms: 2-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• CAS NO: 35023-63-3
• Molecular Weight: 454.431
• Mol File: 35023-63-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside(35023-63-3)
• EPA Substance Registry System: 2-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside(35023-63-3)

Safety Data

• Hazardous Substances Data: 35023-63-3(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 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 
• 6092-24-6 2-methoxybenzoyl-β-D-glucopyranoside 

Relevant articles and documents

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.

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

STEREOSELECTIVITY OF REACTIONS AT THE GLYCOSYDIC CENTER OF CARBOHYDRATES. V. SYNTHESIS OF 1,2-TRANS-ARYLGLYCOSIDES BY THE HELFERICH METHOD USING CATALYSIS BY ORTHOPHOSPHORIC ACID

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