139534-87-5

Upstream product

• 56341-65-2 Benzyl 4,6-O-benzylidene-β-D-galactopyranoside 
• 139534-83-1 (2S,4S,5R,6S)-5-Acetylamino-4-benzoyloxy-2-ethoxythiocarbonylsulfanyl-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 78727-67-0 benzyl 6-O-benzyl-β-D-galactopyranoside 
• 139534-84-2 C₂₇H₂₆O₈ 
• 100740-76-9 1,2,3,4-tetra-O-benzoyl-β-D-galactopyranose 
• 139574-31-5 C₆H₁₂O₅SC₂H₄(C₇H₄O)3 
• 73960-72-2 methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 
• 93-97-0 benzoic acid anhydride 
• 139574-38-2 (2R,4S,5R,6S)-5-Acetylamino-4-benzoyloxy-2-bromo-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 139574-36-0 (2R,4S,5R,6S)-5-Acetylamino-2,4-bis-benzoyloxy-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 

Downstream Products

• 1616503-09-3 1-C-[methyl(5-acetamido-2,6-anhydro-7,8,9-tri-O-benzoyl-3,5-dideoxy-D-glycero-α-D-galacto-nonulosyl)-3-enoate]cyclohexanol 

Relevant academic research and scientific papers

A light- And heat-driven glycal diazidation approach to nitrogenous carbohydrate derivatives with antiviral activity

The aminated mimetics of 2-keto-3-deoxy-sugar acids such as the anti-influenza clinical drugs oseltamivir (Tamiflu) and zanamivir (Relenza) are important bioactive molecules. Development of synthetic methodologies for accessing such compound collections is highly desirable. Herein, we describe a simple, catalyst-free glycal diazidation protocol enabled by visible light-driven conditions. This new method requires neither acid promoters nor transition-metal catalysts and takes place at ambient temperature within 1-2 hours. Notably, the desired transformations could be promoted by thermal conditions as well, albeit with lower efficacy compared to the light-induced conditions. Different sugar acid-derived glycal templates have been converted into a range of 2,3-diazido carbohydrate analogs by harnessing this mild and scalable approach, leading to the discovery of new antiviral agents. This journal is

α-Selectivity and glycal formation are temperature dependent in glycosylation with sialic acid. Synthesis of a Neu5Acα(2-6)Gal thioglycoside building block

The glycosylation with the N-acetylneuraminic acid (Neu5Ac) donor 1 of the 6-OH position of D-galactose in various nitriles promoted by methylsulfenyl triflate at different temperatures is reported. The proportion of α-sialoside increased and glycal 5 decreased at lower temperatures. A short route to a Neu5Acα(2-6)Gal thioglycoside building block is also described.

Glycosylation with sialic acid at HO-3 of three different O-protected D-galactosides in acetonitrile/dichloromethane at low temperature

Three different O-protected D-galactosides have been compared as acceptors in α-sialoside synthesis using glycosyl donor 1, methylsulfenyl triflate as promoter, and acetonitrile/dichloromethane as solvent at -70°C. The 6-O-benzylated acceptor 2 was the most efficient, the α(2-3)sialoside 5 was obtained in 39% isolated yield.