4356-79-0

Upstream product

• 4356-80-3 methyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 529493-92-3 2-(acetoxymethyl)-6-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 108-24-7 acetic anhydride 
• 19488-61-0 methyl 2,3,4,6-tetra-O-benzyl α-D-glucopyranoside 
• 13035-24-0 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 67583-56-6 Methyl 2,3,4-O-tri-O-benzyl-6-O-triphenylmethyl-β-D-glucopyranoside 
• 709-50-2 methyl beta-D-glucopyranoside 
• 67412-01-5 Methyl 6-O-triphenylmethyl-β-D-glucopyranoside 
• 100-44-7 benzyl chloride 
• 6988-40-5 methyl 2,3-di-O-benzyl-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 

Downstream Products

• 82231-38-7 methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 20771-12-4 methyl 6-O-acetyl-β-D-glucopyranoside 
• 51897-71-3 4-O-acetyl-methyl β-D-glucopyranoside 

Relevant academic research and scientific papers

H-bonding activation in highly regioselective acetylation of diols

H-bonding activation in the regioselective acetylation of vicinal and 1,3-diols is presented. Herein, the acetylation of the hydroxyl group with acetic anhydride can be activated by the formation of H-bonds between the hydroxyl group and anions. The reaction exhibits high regioselectivity when a catalytic amount of tetrabutylammonium acetate is employed. Mechanistic studies indicated that acetate anion forms dual H-bonding complexes with the diol, which facilitates the subsequent regioselective monoacetylation.

Temperature-controlled regioselectivity in the reductive cleavage of p-methoxybenzylidene acetals

The regioselective ring opening of pyranosidic 4,6-p-methoxybenzylidene acetals with BH3/Bu2BOTf in THF can be tuned by adjusting the reaction temperature and reagent concentrations. Reductive cleavage at 0 °C resulted in the exclusive formation of 4-O-p-methoxybenzyl (PMB) ethers, whereas reaction at -78 °C produced 6-O-PMB ethers in high yields. The latter condition was observed to be compatible with a variety of acid-sensitive functional groups, including allyl and enol ethers. The presence of water does not interfere with reductive ring opening and may contribute toward in situ generation of H+ as a catalyst for 6-O-PMB ether formation. Reductive cleavage under rigorously aprotic conditions is greatly decelerated, and yields only the 4-O-PMB ether. The temperature-dependent reductive cleavage of the 4,6-acetal can be described in terms of kinetic versus thermodynamic control: Lewis-acid coordination of the more accessible O-6 is favored at higher temperatures, whereas protonation of the more basic but sterically encumbered O-4 predominates at low temperatures.

Selective 6-O-Debenzylation of mono- and disaccharide derivatives using ZnCl2-Ac2O-HOAc

Freshly fused ZnCl2 in Ac2O/HOAc at room temperature has been used for 6-O-debenzylation of mono- and disaccharide derivatives giving yields more than 80%. Notably, allyl, acetyl, benzoyl, tosyl, thiono groups are unaffected under th

SYNTHESIS OF METHYL 2-O-, 3-O-, 4-O-, 6-O-, 2,3-DI-O- AND 4,6-DI-O-β-D-GALACTOPYRANOSYL-β-D-GLUCOPYRANOSIDE

Synthesis of methyl O-β-D-galactopyranosyl-(1->2)-β-D-glucopyranoside 1, methyl O-β-D-galactopyranosyl-(1->3)-β-D-glucopyranoside 2, methyl O-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside 3, methyl O-β-D-galactopyranosyl-(1->6)-β-D-glucopyranoside 4, me

The function of the 5-hydroxymethyl group of lactose in enzymatic hydrolysis with beta-galactosidase from E. coli.

A series of 6-substituted methyl lactoside derivatives together with methyl allolactoside and (6S)-methyl [6-2H]lactoside have been synthesized and characterized by NMR spectroscopy. All compounds were tested as substrates for the enzyme beta-galactosidas

Catalytic transfer hydrogenation of benzylic and styryl compounds with palladium/carbon and 2-propanol. Selective removal of O-benzyl groups from carbohydrate derivatives

2-Propanol is shown to be an effective hydrogen donor, in the presence of palladium/carbon, for catalytic transfer hydrogenation reactions of benzylic and styryl compounds, e.g., for the quantitative conversion of cinnamyl alcohol into 3-phenylpropanol.In the reduction of derivatives of cinnamic acid, decarboxylation also occurs.During the latter reaction, the phenyl group appears to function as an anchoring group for the palladium atom, because derivatives of phenylpropanoic acid are decarboxylated more readily than are those of phenylacetic acid.In hydrogenolysis reactions, aryl alcohols undergo disproportionation whereas benzyl ethers, represented by O-benzyl and related derivatives of carbohydrates, are smoothly cleaved.Although 2-propanol is less reactive as a hydrogen donor than formic acid, it exhibits greater selectivity, as illustrated by relative rates of hydrogenolysis of O-benzyl and O-benzylidene substituents.The use of alumina-supported palladium is more effective than palladium/carbon for promoting stepwise removal of O-benzyl substituents, as shown by the preparation of methyl 2-O-benzyl- and -3-O-benzyl-α-D-glucopyranoside from the 2,3-di-O-benzyl derivative.A possible relationship between the orientation of O-benzyl groups and the chemical shift differences between the diastereotopic benzylic protons is decribed.

A Study of the Rapid Anomerization of Poly-O-benzyl-β-D-glucopyranosides with Titanium Tetrachloride

Titanium tetrachloride rapidly anomerizes methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside in dichloromethane at 25 deg C.Evidence for the proposal that the benzyloxymethyl group on C-5 and the ring oxygen of the glucoside cooperate to prompt the reaction is described.The reagent anomerizes the interglycosidic linkage of several disaccharide derivatives.