191226-99-0

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 86087-23-2 (S)-3-hydroxytetyrahydrofurane 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 178153-11-2 (S)-tetrahydrofuran-3-yl carbonochloridate 

Downstream Products

• 191227-01-7 tert-butyl (4S)-4-N-((S)-tetrahydrofuran-3-yloxycarbonylamino)-2-chloro-5-phenyl-3-oxo-pentanoate 
• 160232-13-3 (2R,3S)-3-N-((S)-tetrahydrofuran-3-yloxycarbonylamino)-2-hydroxy-1-N-(isobutyl)amino-4-phenylbutane 
• 160232-69-9 (2S,3S)-1-chloro-2-hydroxy-3-N-((S)-tetrahydrofuran-3-yloxycarbonylamino)-4-phenylbutane 
• 191227-02-8 (3S)-1-chloro-2-oxo-3-N-((S)-tetrahydrofuran-3-yloxycarbonylamino)-4-phenylbutane 
• 160231-69-6 4-nitro-N-((2R(syn),3S)-2-hydroxy-4-phenyl-3-((S)-tetrahydrofuran-3-yloxycarbonylamino)-butyl)-N-isobutylbenzenesulfonamide 
• 160232-70-2 (1S,1'S)-1-(1'-N-((S)-tetrahydrofuran-3-yloxycarbonylamino)-2'-phenyl)ethyloxirane 
• 191227-00-6 tert-butyl (4S)-4-N-((S)-tetrahydrofuran-3-yloxycarbonylamino)-5-phenyl-3-oxo-pentanoate 

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.

Process for producing 3-amino-2-oxo-1-halogenopropane derivatives

Compounds formed by reacting a protected amino acid with an alkali metal enolate of an alkyl acetate are reacted with a halogenating agent for halogenation of the 2-position, or a protected amino acid is reacted with an alkali metal enolate of an alkyl halogenoacetate, to form a 4-amino-3-oxo-2-halogenobutanoic acid ester derivative, and hydrolysis and decarboxylation are conducted to produce a 3-amino-2-oxo-1-halogenopropane derivative or its salt. The present method is a useful process for producing a 3-amino-2-oxo-1-halogenopropane derivatives which can easily be converted to a 3-amino-1,2-epoxypropane.