158380-44-0

Upstream product

• 150323-06-1 (S)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-pent-4-en-1-one 
• 165883-49-8 (2R,4S)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-4-hydroxy-5-iodo-pentan-1-one 
• 141018-37-3 (3aS,8aR)-2,2-dimethyl-3-(3-phenylpropanoyl)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazole 
• 70987-78-9 (S)-Glycidyl tosylate 

Relevant academic research and scientific papers

Cyclic imidate salts in acyclic stereochemistry: Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides

Reaction of 2-alkyl-4-enamides with I+ and aqueous sodium bicarbonate results in the diastereoselective formation of the corresponding iodohydrins with essentially no iodolactone by-product. The reaction appears to proceed through a cyclic imidate type intermediate. This methodology has been successfully employed for the synthesis of the epoxide intermediate of the orally active HIV-1 protease inhibitor MK-639 (indinavir sulfate).

Highly Diastereoselective Reaction of a Chiral, Non-Racemic Amide Enolate with (S)-Glycidyl Tosylate. Synthesis of the Orally Active HIV-1 Protease Inhibitor L-735,524

Reaction of chiral amide enolate Li-1 with (S)-glycidyl tosylate 11 affords the epoxide 3 in 72percent yield with high diastereoselectivity.Epoxide 3 is converted to the orally-active HIV-1 protease inhibitor L-735,524 in 71percent isolated yield.