1295541-47-7

Upstream product

• 1253943-82-6 methyl 2,6-anhydro-3,4-di-O-benzyl-5-deoxy-D-lyxohex-5-enonate 
• 1295541-45-5 methyl 2,6-anhydro-3,4-di-O-benzyl-5-deoxy-5-nitro-D-lyxohex-5-enonate 
• 868-85-9 Dimethyl phosphite 
• 58871-10-6 3,4-di-O-benzyl-D-glucal 
• 207564-33-8 (2S,3S,4R)-3,4-Bis-benzyloxy-3,4-dihydro-2H-pyran-2-carbaldehyde 

Downstream Products

• 1295541-48-8 methyl (6R)-2,6-anhydro-3,4-di-O-benzyl-5-deoxy-6-(dimethoxyphosphoryl)-5-acetamido-D-gluconate 

Relevant academic research and scientific papers

Accessing C-1 phosphonylated 2-acylamino uronic acids via 2-nitro-glycals

Two approaches are described for the synthesis of 2-acylamino uronic acid glycosyl phosphonates from readily accessible d-glucal. The first approach that entailed oxidation of the C-6 hydroxyl group followed by phosphonylation of the uronate 2-nitro-glycal, resulted in the formation of the β-l-gulo- configured phosphonate. Reversing the reaction order resulted in the exclusive formation of the β-d-gluco-configured phosphonate. In both cases the thermodynamic 1,2-trans-di-equatorial phosphonylation product is obtained.