486407-82-3

Upstream product

• 315718-82-2 (2S,3S)-2-benzyloxymethyl-3-[3-(4-methoxybenzyloxy)-propenyl]-oxirane 
• 315718-84-4 (2R,3R)-3-amino-1-benzyloxy-6-(4-methoxybenzyloxy)-4(E)-hexen-2-ol 
• 100-39-0 benzyl bromide 
• 108-24-7 acetic anhydride 
• 315718-95-7 (2S,3R)-2-benzyloxymethyl-3-[3-(4-methoxybenzyloxy)-1(E)-propenyl]aziridine 

Downstream Products

• 315719-08-5 (2R,3R)-2-amino-1-benzyloxy-6-(4-methoxybenzyloxy)-4(E)-hexen-3-ol 
• 315719-04-1 (1R,2R)-N-[1-benzyloxymethyl-2-hydroxy-5-(4-methoxy-benzyloxy)-3-(E)-pentenyl]-acetamide 

Relevant academic research and scientific papers

A regio- and stereodivergent route to all isomers of vic-amino alcohols.

Vicinal amino alcohols are substructures in several important natural products. They are also frequently employed ligands in asymmetric synthesis. Many enantioselective syntheses of vic-amino alcohols have been reported, but each structure has required its own synthetic route. This study presents a synthetic strategy leading to all eight possible isomers of a given beta-amino alcohol, starting from vinyl epoxides. The developed strategy focuses on the propensity of vinyl epoxides and vinylaziridines to be selectively ring-opened at the allylic position by suitable hard nucleophiles. Within this strategy, a novel large-scale aminolysis reaction and the synthesis of a trisubstituted N-H vinylaziridine are detailed.

A regio-and stereodivergent synthesis of vic-amino alcohols

(Matrix presented) A regio-and stereodivergent synthesis of vic-amino alcohols starting from vinylepoxides is described. The developed strategy focuses on the propensity of vinylepoxides and vinylaziridines to be ring-opened at the allylic position by sui