57472-05-6

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 108-24-7 acetic anhydride 
• 7216-69-5 methyl β-D-lactopyranoside 
• 137119-40-5 methyl 4-O-(4,6-O-benzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 

Downstream Products

• 129905-23-3 methyl 2,3,6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-4-O-benzoyl-6-bromo-6-deoxy-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 99322-24-4 Methyl O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-(1->6)-O-(2,3-di-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 
• 52538-55-3 methyl 2,3,6,2',3',4'-hexa-O-acetyl-6'-O-triphenylmethyl-β-maltoside 
• 116217-62-0 Benzoic acid (2S,3S,4S,5R,6S)-4,5-diacetoxy-2-bromomethyl-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

FeCl3 mediated arylidenation of carbohydrates

Glycosides and thioglycosides based on monosaccharides in reaction with benzaldehyde dimethylacetal or p-methoxybenzaldehyde dimethyl acetal undergo FeCl3-catalyzed (20 mol %) regioselective 4,6-O-arylidenation producing the corresponding acetals in high yields. FeCl3 also mediates acetalation of glycosides and thioglycosides of cellobiose, maltose, and lactose affording the corresponding 4′,6′-O-benzylidene acetals, which were isolated after their acetylation in situ with acetic anhydride and pyridine. The combined yields (two steps) of these final products are also high (61-84%). The procedure is applicable to a wide variety of functional groups including -OBn.

Chemical synthesis using enzymatically generated building units for construction of the human milk pentasaccharides sialyllacto-N-tetraose and sialyllacto-N-neotetraose epimer

α,2-3- and α,2-6-sialylated lactosaminide precursor structures obtained by various enzymatic procedures could be used for glycosylations employing triflic acid/N-iodosuccinimide. Easily accessible selectively protected lactoside derivatives served as acce