57764-18-8

Upstream product

• 4753-07-5 α-hepta-O-acetylmaltosyl bromide 
• 100-51-6 benzyl alcohol 
• 5328-50-7 D-cellobiose octaacetate 
• 3616-19-1 lactose octaacetate 
• 5160-10-1 2,3,6-tetra-O-acetyl-4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-D-glucopyranosylbromide 
• 18464-08-9 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-D-glucopyranose 
• 69308-57-2 Acetic acid (3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-bromo-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 

Downstream Products

• 6992-65-0 benzyl α,β-cellobioside 
• 62746-91-2 C₆₈H₇₀O₁₁ 
• 642441-84-7 benzyl α,β-lactoside 
• 219953-93-2 benzyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 219953-95-4 benzyl O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 219953-91-0 benzyl-{O⁴-[O⁴,O⁶-((R)-benzylidene)-α-D-glucopyranosyl]-β-D-glucopyranoside} 

Relevant academic research and scientific papers

Regioselective removal of the anomeric O-benzyl from differentially protected carbohydrates

A mild, regioselective deprotection of the anomeric O-benzyl from multi-functionally protected carbohydrates via catalytic transfer hydrogenation is described. The protocol is tolerant of O-benzyl and O-benzylidene protections at non-anomeric positions, g

Simple preparations of alkyl and cycloalkyl α-glycosides of maltose, cellobiose, and lactose

Alkyl, cycloalkyl, allyl, 4-pentenyl, and benzyl α-glycosides of maltose, cellobiose, and lactose were prepared via direct reaction of the free bioses with a binary AcBr-AcOH system, followed by glycosidation with alcohol using FeCl3 in MeNO2 or CH2Cl2, Zemple?n deacetylation, and the chromatographic resolution of the mixture. The respective β-biosides were obtained via the glycosidation in MeCN. Alkyl, cycloalkyl, allyl, 4-pentenyl, and benzyl α-glycosides of maltose, cellobiose, and lactose were prepared (17-77% yield; α/β = 70/30-96/4) via a direct reaction of the free disaccharides with a binary AcBr-AcOH mixture, followed by glycosidation with alcohol using FeCl3 in MeNO2 or CH2Cl2, Zemple?n deacetylation, and resolution of the anomeric mixture of glycosides by chromatography. Using MeCN as solvent for the glycosidation step, the corresponding β-biosides were also prepared (16-61% yield; α/β = 25/75-5/95).

Dehydrative glycosylation by diethylaminosulfur trifluoride (DAST) - tin(II) trifluoromethanesulfonate-tetrabutylammonium perchlorate - triethylamine system

Dehydrative glycosylation using 2,3,4,6-tetra-O-benzyl-D-glucopyranose was carried out by the use of a condensing reagent system composed of diethylaminosulfur trifluoride (DAST), tin(II) triflate, tetrabutylammonium perchlorate, and triethylamine. Using this system, two tetrasaccharides, O- a-D-glucopyranosyl-(1→4)-O-α-D-glucopyranosyl-(1→3)-Oα-D-glucopyranosyl- (1→4)-D-glucopyranose and O-a-D-glucopyranosyl-(1→3)-O-α-D- glucopyranosyl-(1→4)-O-α-D-glucopyranosyl-(1→4)-D-glucopyranose, were synthesized.