737767-64-5

Upstream product

• 737767-63-4 (3S,4aS,8aS)-2-((4R,5R)-4-Benzyl-2-oxo-oxazolidin-5-ylmethyl)-decahydro-isoquinoline-3-carboxylic acid tert-butylamide 
• 1014685-49-4 (3S,4aS,8aS,2'R,3'R)-2-[3'-azido-2'-hydroxy-4'-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide 
• 737767-61-2 (3S,4aS,8aS)-2-[2-((R)-Toluene-4-sulfinyl)-ethyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide 
• 128019-40-9 (3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide 

Relevant academic research and scientific papers

Stereocontrolled synthesis and biological activity of two diastereoisomers of the potent HIV-1 protease inhibitor saquinavir

A general enantioselective synthesis of new syn-hydroxyethylamine isosteres has been developed. The approach, based on the controlled opening of functionalized optically active 2,3-epoxy amines, can be conveniently used for the preparation of new peptidom

Stereocontrolled synthesis of hydroxyethylamine isosteres via chiral sulfoxide chemistry

A novel synthesis of enantiopure hydroxyethylamine isosteres 1 has been developed. Reaction of lithiated β-sulfinylethylamines 3 with N-Cbz-imines generated in situ from α-amino-sulfones 4 afforded in good to excellent yields and moderate stereocontrol the 2-sulfinyl-1,3-diamines 2. The latter were submitted to the nonoxidative Pummerer reaction (NOPR) in CH2Cl 2, that produced the target compounds 1 in very good yields with inversion of configuration. In some cases, the use of acetonitrile as solvent resulted in a double-inversion pathway, leading for example to the oxazolidinone 5. The total synthesis of an epimer of Saquinavir has been achieved by this method.