150323-06-1

Upstream product

• 141018-37-3 (3aS,8aR)-2,2-dimethyl-3-(3-phenylpropanoyl)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazole 
• 107-05-1 3-chloroprop-1-ene 
• 106-95-6 allyl bromide 

Downstream Products

• 166740-50-7 (S)-4-[(2S,4R)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-hydroxy-5-oxo-pentyl]-3-tert-butylcarbamoyl-piperazine-1-carboxylic acid tert-butyl ester 
• 150378-17-9 indinavir 
• 150323-38-9 [14C]-N-Dealkyl Indinavir 
• 158380-44-0 (R)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-(R)-oxiranyl-propan-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 
• 158512-24-4 (R)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-(S)-oxiranyl-propan-1-one 

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).

Diastereoselective Syn-epoxidation of 2-alkyl-4-enamides to epoxyamides: Synthesis of the Merck HIV-1 protease inhibitor epoxide intermediate

Reaction of 2-alkyl-4-enamides 2, 9-15 with NIS and aqueous sodium bicarbonate results in the diastereoselective formation of the corresponding iodohydrins 3, 16-22 with essentially no iodolactone by-product. This methodology has been successfully employe

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.