1374561-91-7

Upstream product

• 923952-61-8 2-azido-2-deoxy-4,6-O-(2-naphthylmethylidene)-β-D-glucopyranosyl benzoate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 1374562-18-1 C₄₇H₄₆BrN₃O₆Si 
• 1374562-17-0 C₃₁H₂₈BrN₃O₆ 
• 1374562-16-9 C₃₁H₂₆BrN₃O₆ 
• 1374562-19-2 2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl trichloroacetimidate 
• 1314746-13-8 1,6-anhydro-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose 
• 108-24-7 acetic anhydride 

Relevant academic research and scientific papers

α-glycosylation by d -glucosamine-derived donors: Synthesis of heparosan and heparin analogues that interact with mycobacterial heparin-binding hemagglutinin

Numerous biomolecules possess α-d-glucosamine as structural component. However, chemical glycosylations aimed at this backbone are usually not easily attained without generating the unwanted β-isomer. We report herein a versatile approach in affording full α-stereoselectivity built upon a carefully selected set of orthogonal protecting groups on a d-glucosaminyl donor. The excellent stereoselectivity provided by the protecting group combination was found independent of leaving groups and activators. With the trichloroacetimidate as the optimum donor leaving group, core skeletons of glycosylphosphatidyl inositol anchors, heparosan, heparan sulfate, and heparin were efficiently assembled. The orthogonal protecting groups were successfully manipulated to further carry out the total syntheses of heparosan tri- and pentasaccharides and heparin di-, tetra-, hexa-, and octasaccharide analogues. Using the heparin analogues, heparin-binding hemagglutinin, a virulence factor of Mycobacterium tuberculosis, was found to bind at least six sugar units with the interaction notably being entropically driven.