347384-41-2

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 347384-24-1 methyl 3-O-acetyl-2-O-acryloyl-4,6-di-O-benzyl-α-D-mannopyranoside 

Downstream Products

• 73045-57-5 methyl 4,6-di-O-benzyl-α-D-mannopyranoside 
• 67671-06-1 (2R)-endo-5-norbornene-2-methanol 

Relevant academic research and scientific papers

Highly stereoselective Diels-Alder reactions achieved on some hexopyranosidic templates

The Diels-Alder reactions of some carbohydrate derivatives, as chiral acrylic esters, with cyclopentadiene proceed highly diastereoselectively to provide the adducts carrying a norbornene carboxylate. By reductive removal of the carbohydrate templates from the adducts, both 2S and 2R-enriched 5-norbornene-2-methanol are obtained.

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.