1328893-52-2

Upstream product

• 26922-49-6 1,2; 5,6-di-O-isopropylidene-3-C-nitromethyl-α-D-allofuranose 
• 38088-36-7 3-C-aminomethyl-1,2:5,6-di-O-isoprolylidene-α-D-allofuranose 
• 1885-14-9 phenyl chloroformate 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 1328893-60-2 (3R)-3'-(2,4-dinitrophenyl)-1,2:5,6-di-O-isopropylidene-spiro(3-deoxy-α-D-allofuranose-3,5'-oxazolidin)-2'-one 
• 1328893-56-6 (3R)-3'-benzyl-1,2:5,6-di-O-isopropylidene-spiro(3-deoxy-α-D-allofuranose-3,5'-oxazolidin)-2'-one 

Relevant academic research and scientific papers

A practical access to glucose- and allose-based (5+5) 3- spiropseudonucleosides from a common intermediate

A practical access to glucose-based and allose-based spirooxazolidinones is reported. The synthetic sequence consisting of TEMPO-catalyzed oxidation of 1,2:5,6-di-O-isopropylidene-α-d-glucofuranose, Henry reaction, and reduction provides amino alcohol with allo-configuration on a multigram scale. Alternatively, water elimination from Henry products followed by a rehydration gives an access to diastereomerically pure glucose-based nitro alcohol which upon reduction provides complementary amino alcohol with gluco-configuration. The latter amino alcohols are transformed into spirooxazolidinones (3-spiropseudonucleosides) via their N-Cbz or N-phenylcarbamate derivatives. The title compounds easily undergo N-derivatization and give highly crystalline materials. Two of the newly obtained (5+5) 3-spiropseudonucleosides are characterized by X-ray crystallography.