77870-95-2

Upstream product

• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 40489-45-0 2-benzyloxycarbonylamino-3-hydroxy-propionic acid benzyl ester 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 21209-51-8 N-benzyloxycarbonyl-L-serine benzyl ester 
• 77667-89-1 1,3-Di-p-tolyl-2-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-isourea 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 59531-24-7 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 1145-80-8 N-(benzyloxycarbonyl)-L-serine 
• 100-39-0 benzyl bromide 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 

Relevant academic research and scientific papers

Visible-light-promoted 3,5-dimethoxyphenyl glycoside activation and glycosylation

A new glycosylation method promoted by visible light with 3,5-dimethoxyphenyl glycoside as the donor was developed. This protocol delivers bothO-glycosides andN-glycosides in moderate to excellent yields using a wide range ofO-nucleophiles and nucleobases as the glycosyl acceptors.

Visible Light Enables Aerobic Iodine Catalyzed Glycosylation

A versatile protocol for light induced catalytic activation of thioglycosides using iodine as an inexpensive and readily available photocatalyst was developed. Oxygen serves as a green and cost-efficient terminal oxidant and irradiation is performed with a common household LED-bulb. The scope of this glycosylation protocol was investigated in the synthesis of O-glycosides with yields up to 95 %.

Glycosylation reaction under high pressure

Glycosylation of various alcohols with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide (1) in the presence of hindered amines under conditions of high pressure gave α-glycosides in good yield with high selectivity.

Un nouvel agent de glycosylation: l'anhydride trifluoromethanesulfonique. Synthese des α et β O-glycosyl-L-serine, -L-threonine et -L-hydroxyproline

When 2,3,4,6-tetra-O-benzyl-D-glucopyranose, -D-galactopyranose and 2,3,4-tri-O-benzyl-D-xylopyranose were allowed to react in the cold in dichloromethane or acetonitrile as solvent in the presence of trifluoromethanesulfonic (triflic) anhydride, with methyl or benzyl esters of the N-(benzyloxycarbonyl)-L-serine, -L-threonine, and -L-hydroxyproline, an anomeric mixture of the corresponding O-glycosylaminoacids was obtained (55 to 90percent overall yield), with the α-anomer being predominant.The same experimental procedure was successfully applied to the condensation of the benzyl ester of the N-(benzyloxycarbonyl)-L-hydroxyproline with 2,3,4-tri-O-benzyl-L-arabinopyranose and 2,3,5-tri-O-benzyl-L-arabinofuranose affording the corresponding condensation products with similar yield.Pure α and β anomers were obtained after column chromatography or crystallization with 30 to 65percent yield.Hydrogenolysis of benzyl derivatives afforded the unprotected compounds.Optical rotation, (1)H and (13)C nmr were the main methods used to assess structure and stereochemistry.