347384-21-8

Upstream product

• 98-88-4 benzoyl chloride 
• 405292-03-7 methyl 2-O-acryloyl-4,6-di-O-benzyl-α-D-mannopyranoside 

Relevant academic research and scientific papers

Highly diastereoselective Diels-Alder reactions of acrylic esters incorporated into a variety of hexopyranosides

The Diels-Alder reactions of a variety of hexopyranosides carrying an acrylic ester with cyclopentadiene were examined. Some acrylic esters provided the cycloaddition products carrying a norbornene carboxylate with a high level of diastereoselectivity. Plausible mechanisms are presented for the cases of a 4-O-acryloyl-6-deoxy-α-D-glucopyranosidic and 2-O-acryloyl-α-D-glucopyranosidic substrates. By reductive removal of the carbohydrate templates from the adducts, either 2S or 2R-enriched 5-norbornene-2-methanol were obtained.