200938-37-0

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 120312-13-2 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl fluoride 
• 151992-76-6 Ethyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 151992-75-5 ethyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside 
• 166516-68-3 ethyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside 
• 200938-30-3 ethyl 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 

Downstream Products

• 129210-15-7 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate 

Relevant academic research and scientific papers

Synthesis of part of a proposed insulin second messenger glycosylinositol phosphate and the inner core of glycosylphosphatidylinositol anchors

Synthesis of 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate, an inner core structure found in various glycosylphosphatidylinositols, and the corresponding 1,2-cyclic phosphate, proposed as part of an insulin second messenger glycosylinositol phosphate, is described. Chirality in the inositol part of the molecule was achieved by the use of a known D-camphor acetal intermediate. The glycosylation used 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl fluoride as glycosyl donor. The allyl group can be chemoselectively removed, opening a route to oligosaccharides bound to the 4-position of the glucosamine unit. The phosphorylation was accomplished by the phosphoramidate procedure.