255912-56-2

Upstream product

• 255912-51-7 Acetic acid (2R,3S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-(4-nitro-phenyl)-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-3,6-dihydro-2H-pyran-3-yl ester 
• 555-16-8 4-nitrobenzaldehdye 

Downstream Products

• 255912-57-3 Acetic acid (2R,3R,4R)-3-hydroxy-2-(4-nitro-phenyl)-3,4-dihydro-2H-pyran-4-yl ester 
• 255912-58-4 Acetic acid (2R,3S,4S,5R)-4,5,6-triacetoxy-2-(4-nitro-phenyl)-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

Asymmetric synthesis of (5S)-4-deoxy-5-C-(4-nitrophenyl)-L-threo-pentose and (5R)-5-C-(4-nitrophenyl)-L-arabinose

In the presence of Eu(fod)3, (1E)-(2',3',4',6'-tetra-O-acetyl-?2-D-glucopyranosyloxy)buta-1,3-diene and its (3Z)-4-O-acetyl derivative undergo Re-face and endo selective hereto Diels-Alder reactions with 4-nitrobenzaldehyde, 5-nitrofuran-2-carbaldehyde and 5-nitrothiophene-2-carbaldehyde. The cycloadducts are converted into the title compounds, early examples of 'free' 5-C-arylpentopyranoses.