191280-97-4

Upstream product

• 35023-80-4 2,3:5,6-di-O-isopropylidene-D-mannose oxime 
• 52085-14-0 4-benzoxy-salicylaldehyde 

Downstream Products

• 320350-81-0 6-benzyloxy-benzofuran 
• 162750-07-4 (S)-N-(6-benzyloxy-2,3-dihydrobenzofuran-3-yl)hydroxylamine 
• 182823-42-3 N-((S)-6-Benzyloxy-2,3-dihydro-benzofuran-3-yl)-N-[(3aS,6R,6aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-hydroxylamine 

Relevant academic research and scientific papers

Enantioselective synthesis of a 5-LO inhibiting hydroxyurea. Construction of the dihydro-benzofuran by tandem nucleophilic addition and intramolecular cyclization

An enantioselective synthesis of a 5-LO inhibiting chiral hydroxyurea is described based on the nucleophilic addition of dimethylsulfoxonium ylide to a nitrone bearing a mannose-derived chiral auxiliary. The dihydrobenzofuran skeleton is then constructed by a spontaneous cyclization of the initial adduct, thus completing a tandem nucleophilic addition-cyclization protocol.

Enantioselective Synthesis of 5-LO Inhibitor Hydroxyureas. Tandem Nucleophilic Addition-Intramolecular Cyclization of Chiral Nitrones

An enantioselective synthesis of chiral hydroxyurea based 5-lipoxygenase inhibitors is reported via a five-step sequence in about 30% overall yield. The synthesis is based on a novel tandem nucleophilic addition-intramolecular cyclization reaction in which a chiral nitrone functions as the electrophilic acceptor species. A mannose-based chiral auxiliary controls the diastereoselectivity of the reaction in an 8:1 ratio. After the auxiliary removal and appropriate functionalization, a single recrystallization afforded the target structures in >99% ee.