160529-97-5

Upstream product

• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 28642-64-0 methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 
• 6748-85-2 methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 98-88-4 benzoyl chloride 
• 76419-48-2 methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside 
• 54769-36-7 N-benzoyloxybenzotriazole 
• 221002-70-6 methyl 2‐O‐benzoyl‐3‐O‐benzyl‐4,6‐O-benzylidene‐α‐D‐glucopyranoside 
• 2641-79-4 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 100-52-7 benzaldehyde 
• 66-99-9 β-naphthaldehyde 
• 93-97-0 benzoic acid anhydride 

Downstream Products

• 160529-98-6 Benzoic acid (2S,3R,4R,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester 
• 58341-68-7 methyl 3,6-di-O-benzyl-α-D-glucopyranoside 
• 221002-89-7 methyl 2,4-di-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,6-di-O-benzyl-α-D-glucopyranoside 
• 160530-00-7 methyl 3,6-di-O-benzyl-4-deoxy-4-fluoro-α-D-galactopyranoside 
• 160530-05-2 methyl O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1<*>2)-4-deoxy-4-fluoro-α-D-galactopyranoside 
• 160530-04-1 methyl O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1<*>2)-3,6-di-O-benzyl-4-deoxy-4-fluoro-α-D-galactopyranoside 

Relevant academic research and scientific papers

Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity

The reactivity of both coupling partners—the glycosyl donor and acceptor—is decisive for the outcome of a glycosylation reaction, in terms of both yield and stereoselectivity. Where the reactivity of glycosyl donors is well understood and can be controlled through manipulation of the functional/protecting-group pattern, the reactivity of glycosyl acceptor alcohols is poorly understood. We here present an operationally simple system to gauge glycosyl acceptor reactivity, which employs two conformationally locked donors with stereoselectivity that critically depends on the reactivity of the nucleophile. A wide array of acceptors was screened and their structure–reactivity/stereoselectivity relationships established. By systematically varying the protecting groups, the reactivity of glycosyl acceptors can be adjusted to attain stereoselective cis-glucosylations.

HClO4-silica-catalysed regioselective opening of benzylidene acetals and its application towards regioselective HO-4 glycosylation of benzylidene acetals in one-pot

Here we report a high-yielding method for the regioselective reductive ring opening of 4,6-O-benzylidene acetals of hexapyranosides using inexpensive and robust HClO4-SiO2 as the acidic catalyst and triethylsilane as the hydride dono

Some observations on the reductive ring opening of 4,6-O-benzylidene acetals of hexopyranosides with the borane trimethylamine-aluminium chloride reagent

Reductive ring openings of 3-O-benzoyl-4,6-O-benzylidene-d-glucopyranosides with BH3·NMe3-AlCl3 are accompanied by side reactions, such as debenzoylation and reduction of the benzoate to benzyl ether. This phenomenon was r

METHOD FOR PREPARING HEXOSE DERIVATIVES

A method for preparing hexose derivatives comprises the steps of providing a silylated hexose, treating the silylated hexose with a first carbonyl compound in the presence of a catalyst to form an ketalized hexose, treating the ketalized hexose with a second carbonyl compound followed by treating with a first reductant to form an etherized hexose, and converting the etherized hexose into a target hexose derivative, which can be 2-alcohol hexose, 3-alcohol hexose, 4-alcohol hexose, or a 6-alcohol hexose. In particular, the present invention can prepare the hexose derivatives with highly regioselective scheme to protect individual hydroxyls of monosaccharide units and install an orthogonal protecting group pattern in a one-pot manner

Synthesis and nmr characterisation of methyl mono- and DI-0-α-L-rhamnopyranosyl-α-d-glucopyranosiduronic acids

The synthesis and NMR characterisation of methyl mono- and di-O-α-L-rhamnopyranosyl-α-D-glucopyranosiduronic acids 1-6 are described. Two commercial starting products were used: methyl α-D-glucopyranoside 7 for the preparation of 1 and 2, and methyl (R)-4,6-O-benzylidene-α-D-glucopyranoside 8 for 3-6. Oxidation reaction of the hydroxymethyl group of glucose to a carboxylic acid group was performed by sodium hypochlorite 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO)-mediated procedure after the coupling reaction. Glycosylation was carried out using the trichloroacetimidate approach with trimethylsilyl trifluoromethanesulfonate (TMSOTf) as promoter, resulting in a completely stereoselective formation of the a glycosyl linkage.

Synthesis of methyl O-α-L-rhamnopyranosyl-(12)-α-D-galactopyranosides specifically deoxygenated at position 3, 4, or 6 of the galactose residue

The title disaccharides were synthesized by condensation of 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl bromide with suitably protected, deoxygenated derivatives of methyl α-D-galactopyranoside.Deoxygenation was achieved via activation of a protected methyl α