76679-49-7

Upstream product

• 47727-93-5 2,3,4-tri-O-benzyl-D-glucopyranose 
• 76679-47-5 methyl-2,3,4-tri-O-benzyl-6-O-trifluoromethanesulfonyl-α-D-glucopyranoside 
• 1200763-23-0 methyl 2,3,4-tri-O-benzyl-6-O-(2',3',4'-tri-O-benzyl-6'-O-levulinoyl-β-D-glucopyranosyl)-1-α-D-glucopyranoside 
• 1415590-78-1 methyl O-(2,3,4-tri-O-benzyl-6-O-picoloyl-β-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 1415590-58-7 ethyl 2,3,4-tri-O-benzyl-6-O-picolinyl-1-thio-β-D-glucopyranoside 
• 87470-73-3 phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 1200763-53-6 methyl 2,3,4-tri-O-benzyl-6-O-[2',3',4'-tri-O-benzyl-6'-O-(2'',3'',4''-tri-O-benzyl-6-O-levulinoyl-β-D-glucopyranosyl)-β-D-glucopyranosyl]-1-β-D-glucopyranoside 
• 4159-55-1 methyl 6-O-(β-D-glucopyranosyl)-α-D-glucopyranoside 

Relevant academic research and scientific papers

6-O-Picolinyl and 6-O-Picoloyl Building Blocks As Glycosyl Donors with Switchable Stereoselectivity

Remote 6-O-picolinyl or 6-O-picoloyl substituents often provide high β-selectivity due to H-bond-mediated aglycone delivery (HAD). Herein it has been demonstrated that if the nitrogen atom of the 6-O-picolinyl or picoloyl moiety is temporarily blocked by coordination to a metal center (Pd), it cannot engage in HAD-mediated β-glycosylation. Hence, the stereoselectivity of 6-O-picolinyl/picoloyl-assisted glycosylations can be "switched" to α-selectivity.

Low-concentration 12-trans β-selective glycosylation strategy and its applications in oligosaccharide synthesis

This study develops an operationally easy, efficient, and general 1,2-trans β-selective glycosylation reaction that proceeds in the absence of a C2 acyl function. This process employs chemically stable thioglycosyl donors and low substrate concentrations to achieve excellent β-selectivities in glycosylation reactions. This method is widely applicable to a range of glycosyl substrates irrespective of their structures and hydroxyl-protecting functions. This low-concentration 1,2-trans β-selective glycosylation in carbohydrate chemistry removes the restriction of using highly reactive thioglycosides to construct 1,2-trans β-glycosidic bonds. This is beneficial to the design of new strategies for oligosaccharide synthesis, as illustrated in the preparation of the biologically relevant β-(1-6)-glucan trisaccharide, β-linked Gb3 and isoGb3 derivatives.

SYNTHESIS OF α- AND β-GLYCOPYRANOSIDES via 1-O-ALKYLATION

1-O-Alkylation of partly protected glucopyranose 1 and galactopyranose 13 led to a convenient, short term synthesis of β-glycosides and β-disaccharides 4a-d and 14.Glucopyranose 2 with a bulky protective group at O-6 yielded exclusively the α-anomer (isomaltoside derivative) 5.