158512-24-4

Usage

Uses

An intermediate in the synthesis of Indinavir.

InChI:InChI=1/C24H27NO3/c1-24(2)25(22-20-11-7-6-10-17(20)14-21(22)28-24)23(26)18(13-19-15-27-19)12-16-8-4-3-5-9-16/h3-11,18-19,21-22H,12-15H2,1-2H3/t18?,19?,21-,22+/m1/s1

Upstream product

• 67843-74-7 (S)-epichlorohydrin 
• 141018-37-3 (3aS,8aR)-2,2-dimethyl-3-(3-phenylpropanoyl)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazole 
• 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 
• 158380-42-8 (2R,4S)-2-Benzyl-5-chloro-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-4-hydroxy-pentan-1-one 
• 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 
• 70987-78-9 (S)-Glycidyl tosylate 

Downstream Products

• 194204-25-6 (2R,4S)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-4-hydroxy-5-(2-methylsulfanyl-phenyl)-pentan-1-one 
• 808149-73-7 (S)-4-Benzyl-3-[(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]-1-(4-methoxy-benzyl)-imidazolidin-2-one 
• 150378-17-9 indinavir 

Relevant academic research and scientific papers

A highly diastereoselective electrochemical epoxidation

The electrochemical epoxidation of 3 gives the Merck HIV-protease inhibitor, Indinavir Sulfate, intermediate 1 in high yield and diastereoselectivity in an operationally simple procedure.

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.