191227-01-7

Upstream product

• 191226-99-0 N-(S)-tetrahydrofuran-3-yloxycarbonyl-L-phenylalanine 
• 178153-11-2 (S)-tetrahydrofuran-3-yl carbonochloridate 
• 191227-00-6 tert-butyl (4S)-4-N-((S)-tetrahydrofuran-3-yloxycarbonylamino)-5-phenyl-3-oxo-pentanoate 

Downstream Products

• 191227-02-8 (3S)-1-chloro-2-oxo-3-N-((S)-tetrahydrofuran-3-yloxycarbonylamino)-4-phenylbutane 
• 160232-70-2 (1S,1'S)-1-(1'-N-((S)-tetrahydrofuran-3-yloxycarbonylamino)-2'-phenyl)ethyloxirane 
• 160231-69-6 4-nitro-N-((2R(syn),3S)-2-hydroxy-4-phenyl-3-((S)-tetrahydrofuran-3-yloxycarbonylamino)-butyl)-N-isobutylbenzenesulfonamide 
• 160232-69-9 (2S,3S)-1-chloro-2-hydroxy-3-N-((S)-tetrahydrofuran-3-yloxycarbonylamino)-4-phenylbutane 
• 160232-13-3 (2R,3S)-3-N-((S)-tetrahydrofuran-3-yloxycarbonylamino)-2-hydroxy-1-N-(isobutyl)amino-4-phenylbutane 

Relevant academic research and scientific papers

New approaches to the industrial synthesis of HIV protease inhibitors

Efficient and industrially applicable synthetic processes for precursors of HIV protease inhibitors (Amprenavir, Fosamprenavir) are described. These involve a novel and economical method for the preparation of a key intermediate, (3S)-hydroxytetrahydrofuran, from L-malic acid. Three new approaches to the assembly of Amprenavir are also discussed. Of these, a synthetic route in which an (S)-tetrahydrofuranyloxy carbonyl is attached to L-phenylalanine appears to be the most promising manufacturing process, in that it offers satisfactory stereoselectivity in fewer steps.