201056-71-5

Upstream product

• 3377-92-2 vinyl pivalate 
• 20701-61-5 ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 3282-30-2 pivaloyl chloride 
• 604-69-3 β-D-glucose pentaacetate 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 7473-36-1 ethyl 1-thio-β-D-glucopyranoside 

Downstream Products

• 382614-48-4 2,2-Dimethyl-propionic acid (2R,4aR,6S,8S,8aR)-6-ethylsulfanyl-7-oxo-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 318954-52-8 2,2-Dimethyl-propionic acid (2R,4aR,6R,8R,8aS)-6-ethylsulfanyl-7-[(Z)-hydroxyimino]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 318954-53-9 C₂₅H₃₅NO₇S 
• 318954-55-1 C₅₁H₆₁NO₁₃ 
• 318954-61-9 C₅₁H₆₁NO₁₃ 
• 382614-54-2 methyl 2,3,4-tri-O-benzyl-6-O-[2-deoxy-2-(O-pivaloyl)oximino-3-O-pivaloyl-4,6-O-benzylidene-1-α-D-glucopyranosyl]-1-O-α-D-glucopyranoside 
• 382614-72-4 methyl 2,3,4-tri-O-benzyl-6-O-[2-deoxy-2-(O-pivaloyl)oximino-3-O-pivaloyl-4,6-O-benzylidene-1-β-D-glucopyranosyl]-1-O-α-D-glucopyranoside 

Relevant academic research and scientific papers

Regioselective C-3-O-acylation and O-methylation of 4,6-O-benzylidene-β-D-gluco- and galactopyranosides displaying a range of anomeric substituents

The regioselective C-3-O-acylation and O-methylation of a range of 4,6-O-benzylidene-β-D-gluco- and galactopyranosides has been studied. Regioselectivity is achieved by forming the copper chelate of the 2,3-diol using either sodium hydride and copper(II) chloride, or copper(II) acetylacetanoate, or copper(II) acetate, prior to introduction of the acylating or methylating agent.

Synthesis of disaccharides containing α-linked GlcNAc or β-linked ManNAc units

The synthesis of disaccharides containing α-linked GlcNAc or β-linked ManNAc units from shelf-stable, and yet highly reactive, 2-oximinoglycosyl donors is described. Access to a preponderance of the disaccharide containing either the α-linked GlcNAc or β-linked ManNAc unit can be obtained by careful choice of solvent and glycosidation conditions.

Regioselective C-3-O-acylation and O-alkylation of 4,6-O-benzylidene-β-D-glucopyranoside derivatives displaying a range of anomeric substituents

Regioselective C-3-O-acylation and O-alkylation of ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside, phenyl 4,6-O-benzylidene-β-D-glucopyranoside and phenyl 4,6-O-benzylidene-1-seleno-β-D-glucopyranoside is described. Regioselectivity is obtained by first treating the benzylidene diols with sodium hydride and copper (II) chloride to form a THF soluble copper chelate.

Regioselective Lipase-catalysed acylation of 4,6-O-benzylidene-α- and - β-D-pyranoside derivatives displaying a range of anomeric substituents

The application of Lipase enzymes to effect regioselective C-3-O- acylation of 4,6-O-benzylidene-β-D-gluco- and -galactopyranosides displaying a range of anomeric substituents, and C-2-O-acylation of phenyl 4,6-O- benzylidene-α-D-glucopyranoside and ethyl 4,6-O-benzylidene-1-thio-α-D- glucopyranoside is reported. In particular this method has allowed introduction of a variety of acyl protecting groups at the C-3 hydroxyl group of ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 11.

Regioselective lipase-catalysed acylation of 4,6-O-benzylidene-β-D-pyranoside derivatives displaying a range of anomeric substituents

The application of lipase enzymes to effect regioselective C-3-O-acylation of 4,6-O-benzylidene-β-D-gluco- and galactopyranosides displaying a range of anomeric substituents is reported. In particular this method has allowed introduction of a variety of acyl protecting groups at the C-3 hydroxyl group of ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 9.