20822-89-3

Basic information

• Product Name: methyl 3,5,6,-tri-O-benzyl-β-D-glucofuranoside
• Synonyms: methyl 3,5,6,-tri-O-benzyl-β-D-glucofuranoside
• CAS NO: 20822-89-3
• Molecular Weight: 464.558
• Mol File: 20822-89-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methyl 3,5,6,-tri-O-benzyl-β-D-glucofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3,5,6,-tri-O-benzyl-β-D-glucofuranoside(20822-89-3)
• EPA Substance Registry System: methyl 3,5,6,-tri-O-benzyl-β-D-glucofuranoside(20822-89-3)

Safety Data

• Hazardous Substances Data: 20822-89-3(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 53928-30-6 1,2-O-isopropylidene-3,5,6-tri-O-benzyl-α-D-glucofuranoside 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 100-39-0 benzyl bromide 
• 161835-09-2 1,2-anhydro-3,5,6-tri-O-benzyl-β-D-mannofuranose 
• 35958-64-6 3,5,6-Tri-O-benzyl-α,β-D-glucofuranose 
• 161835-13-8 1,2-anhydro-3,5,6-tri-O-benzyl-α-D-glucofuranose 

Downstream Products

• 89733-69-7 methyl-3,5.6-tri-O-benzyl-2-O-(methoxycarbonylmethyl)-β-D-glucofuranoside 
• 78582-31-7 methyl 3,5,6-tri-O-benzyl-2-O-(2,3-epoxypropyl)-β-D.glucofuranoside 
• 78582-34-0 methyl 3,5,6-tri-O-benzyl-2-O-(2-hydroxyethyl)-β-D-glucofuranoside 
• 78582-29-3 methyl 3,5,6-tri-O-benzyl-2-O-(2-hydroxypropyl)-β-D-glucofuranoside 
• 89733-67-5 3,5,6-tri-O-benzyl-1-O-methyl-1,2-O-(1,2-ethanediyl)-4-O-(trichlorocarbamyl)-D-glucose 
• 78582-37-3 3,5.6-tri-O-benzyl-1,2-O-(1,2-ethanediyl)-α-D-glucofuranose 
• 78582-36-2 3,5,6-tri-O-benzyl-1-O-methyl-1,2-O-(1,2-ethanediyl)-D-glucose 
• 78582-33-9 (3R,6R,7S)-7-Benzyloxy-6-((R)-1,2-bis-benzyloxy-ethyl)-3-methyl-hexahydro-furo[2,3-b][1,4]dioxine 
• 78582-33-9 (3S,6R,7S)-7-Benzyloxy-6-((R)-1,2-bis-benzyloxy-ethyl)-3-methyl-hexahydro-furo[2,3-b][1,4]dioxine 
• 78582-32-8 (1S,2R,3R)-1,3,4-Tris-benzyloxy-1-((3S,5S)-3-methoxy-5-methyl-[1,4]dioxan-2-yl)-butan-2-ol 
• 125365-20-0 Methyl 3,5,6-tri-O-benzyl-1,2-O-(2-tetrahydropyranyloxyethyl)-β-<*>-glucofuranoside 
• 125365-35-7 Methyl 3,5,6-tri-O-benzyl-2-O-(2-tetrahydropyranyloxyethoxy)ethyl-β-<*>-glucofuranose 
• 125365-32-4 3,5-Di-O-benzyl-1,2-O-ethylene-α-<*>-glucofuranose 
• 28069-78-5 1,2-O-Ethylene-α-<*>-glucofuranose 3,5,6-triacetate 

Relevant articles and documents

A Warburg effect targeting vector designed to increase the uptake of compounds by cancer cells demonstrates glucose and hypoxia dependent uptake

Glycoconjugation to target the Warburg effect provides the potential to enhance selective uptake of anticancer or imaging agents by cancer cells. A Warburg effect targeting group, rationally designed to facilitate uptake by glucose transporters and promote cellular accumulation due to phosphorylation by hexokinase (HK), has been synthesised. This targeting group, the C2 modified glucose analogue 2-(2-[2-(2-aminoethoxy)ethoxy]ethoxy)-D-glu-cose, has been conjugated to the fluorophore nitrobenzoxadiazole to evaluate its effect on uptake and accumulation in cancer cells. The targeting vector has demonstrated inhibition of glucose phosphorylation by HK, indicating its interaction with the enzyme and thereby confirming the potential to facilitate an intracellular trapping mechanism for compounds it is conjugated with. The cellular uptake of the fluorescent analogue is dependent on the glucose concentration and is so to a greater extent than is that of the widely used fluorescent glucose analogue, 2-NBDG. It also demonstrates selective uptake in the hypoxic regions of 3D spheroid tumour models whereas 2-NBDG is distributed primarily through the normoxic regions of the spheroid. The increased selectivity is consistent with the blocking of alternative uptake pathways.

Synthesis and glycosidic reaction of 1,2-anhydromanno-, lyxo-, gluco-, and xylofuranose perbenzyl ethers

Stereospecific synthesis of 1,2-anhydromanno-, lyxo-, gluco-, and xylofuranose perbenzyl ethers was successfully achieved via intramolecular SN2 reaction of the corresponding C-1 alkoxide with C-2 bearing tosyloxy group. The key intermediates, furanose 2-sulfonates, were prepared from the corresponding 1,2-diols and tosyl chloride under phase transfer conditions in good yields. Condensation of the anhydro sugars with 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose or N-benzyloxycarbonyl L-serine methyl ester in the absence of catalyst gave 1,2-trans-linked glycofuranosides in high yield.

ACID-CATALYZED CONVERSION OF 2-O-(2-HYDROXYPROPYL)-D-GLUCOSE DERIVATIVES INTO 1,2-O-(1-METHYL-1,2-ETHANEDIYL)-D-GLUCOSE ACETALS. STUDIES RELATED TO O-(2-HYDROXYPROPYL)CELLULOSE

The acid-catalyzed solvolysis of methyl 3,5,6-tri-O-benzyl-2-O-(2-hydroxypropyl)-α-D-glucofuranoside (1) in chloroform involves a neighboring-group attack on C-1 by the hydroxypropyl substituent, and opening of the furanoside ring to yield a diastereomeric pair of 3,5,6-tri-O-benzyl-1-Omethyl-1,2-O-(1-methyl-ethanediyl)-D-glucose acetals (2 and 3).The latter, which differ in configuration at C-8,represent a resolution of the enantiomeric forms of the original 2-O-(2-hydroxypropyl) group.In a succeeding reaction, the 1-methoxyl group of each acetal undergoes an intramolecular displacement by O-4, leading to the formation of the corresponding biycyclic acetals, i.e., the two diastereomers (4 and 5) of 3,5,6-tri-O-benzyl-1,2-O-(1-methyl-1,2-ethanediyl)-α-D-glucofuranose.Solvolysis of 6, the β anomer of 1, proceeds in an analogous manner, although more rapidly, to yield a corresponding pair of acyclic-aldose acetals (7 and 8), as well as bicyclic acetals 4 and 5.Similar results are observed for solvolysis in the 2-O-(2-hydroxyethyl) series, whereas the reaction of the 2-O-(2,3-epoxypropyl) counterpart of 1 (or 6) with hydrogen chloride affords the corresponding chloromethyl analogs of 4 and 5.In all of these series, one of each diastereomeric pair of products is more stable than the other, and reasons for this are considered.Evidence based on n.m.r.-spectral data and steric factors is presented to show that the configuration of the chiral center C-8 of 2, 4, and 7 is (S), whereas it is (R) in 3, 5, and 8.Also, conformational characteristics of the various solvolysis products are assessed, and mechanisms possibly involved in their formation are discussed.