35303-87-8

Upstream product

• 108-24-7 acetic anhydride 
• 100-44-7 benzyl chloride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 35303-86-7 (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol 
• 709-50-2 methyl beta-D-glucopyranoside 
• 82231-35-4 methyl 2,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 82231-34-3 methyl 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-glucopyranoside 

Downstream Products

• 35303-86-7 (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol 
• 64694-19-5 methyl 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl-α-(1→3)-2,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 92812-57-2 methyl 2,4,6-tri-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl)-α-D-glucopyranoside 

Relevant academic research and scientific papers

Streamlined access to carbohydrate building blocks: Methyl 2,4,6-tri-O-benzyl-α-D-glucopyranoside

Presented herein is an improved synthesis of a common 3-OH glycosyl acceptor. This compound is a building block that is routinely synthesized by many research groups to be used in glycosylation refinement studies. The only known direct synthesis by Koto lacks regioselectivity and relies on chromatography separation using hazardous solvents. Our improved synthetic approach relies on Koto's selective benzylation protocol, but it is followed by acylation-purification-deacylation sequence. Although this approach involves additional manipulations, it provides consistent results and is superior to other indirect strategies. Also obtained, albeit in minor quantities, is 4-OH acceptor, another common building block.

Ceric ammonium nitrate/acetic anhydride: A tunable system for the O-acetylation and mononitration of diversely protected carbohydrates

Esterification of a wide range of partially protected carbohydrate derivatives was achieved using acetic anhydride and a catalytic amount of ceric ammonium nitrate (CAN). Compatibility with the commonly used protecting groups was demonstrated, with the es

A STEREOSELECTIVE α-GLUCOSYLATION BY USE OF A MIXTURE OF 4-NITROBENZENESULFONYL CHLORIDE, SILVER TRIFLUOROMETHANESULFONATE, N,N-DIMETHYLACETAMIDE, AND TRIETHYLAMINE

Stereoselective α-glucosylation of partially protected carbohydrates with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose in dichloromethane, in the presence of a quaternary mixture of 4-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, N,N-dimethylacetamide, and triethylamine gave O-α-D-glucopyranosyl-(1->4)- and -(1->6)-2-acetamido-2-deoxy-D-glucopyranose (N-acetylmaltosamine and N-acetylisomaltosamine).A step-by-step synthesis of O-α-D-glucopyranosyl-(1->4)-O-6)>-D-glucopyranose is described.

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.