146626-70-2

Upstream product

• 545-06-2 trichloroacetonitrile 
• 501-53-1 benzyl chloroformate 
• 503180-93-6 4-pentenyl 6-O-acetyl-3,4-di-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranoside 
• 503180-92-5 4-pentenyl 3,4-di-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranoside 
• 503180-90-3 4-pentenyl 2-amino-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside 

Downstream Products

• 146626-72-4 4-O-(6-O-Acetyl-2-benzyloxycarbonylamino-2-deoxy-3,4-di-O-benzyl-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 

Relevant academic research and scientific papers

Toward the automated solid-phase synthesis of oligoglucosamines: Systematic evaluation of glycosyl phosphate and glycosyl trichloroacetimidate building blocks

Glucosamines are common components of many biologically important oligosaccharides. Reported is a systematic evaluation of glucosamine phosphates and trichloroacetimidates as glycosylating agents for the efficient construction of β-(1→6) glucosamine linkages. A set of differentially protected glucosamine donors incorporating a host of amine protecting groups, including 2-phthaloyl, benzyloxycarbonyl (Z), trichloroetheoxycarbonyl (Troc) and trichloroacetyl (TCA) protective groups, were prepared. Donors were initially evaluated for reactivity and protecting group compatibility in a solution-phase study with a model 6-hydroxyl galactose acceptor. Based on these results, glucosamine donor 10 was selected for the solution-phase synthesis of a β-(1→6)-glucosamine pentasaccharide. Finally, building block 10 proved well suited for use in the automated solid-phase synthesis of a repeating unit trisaccharide. An assessment of glucosamine phosphate donors as potential glycosylating agents for a variety of glucosamine linkages is also discussed.

An Expeditious and Stereocontrolled Preparation of 2-Azido-2-deoxy-β-D-glucopyranose Derivatives from D-Glucal

1,6-Anhydro-2-azido-2-deoxy-β-D-glucopyranose has been prepared by a two-step procedure from D-glucal and transformed into precursors useful in the synthesis of oligosaccharides.