160232-70-2

Upstream product

• 178153-11-2 (S)-tetrahydrofuran-3-yl carbonochloridate 
• 160232-69-9 (2S,3S)-1-chloro-2-hydroxy-3-N-((S)-tetrahydrofuran-3-yloxycarbonylamino)-4-phenylbutane 
• 160232-67-7 (2S,3S)-3-Amino-1-chloro-4-phenyl-butan-2-ol 
• 123054-12-6 (2S)-N,N-dibenzylphenylalaninal 
• 143601-45-0 (S)-tert-butyl 4-<(benzyloxycarbonyl)amino>-3-oxo-5-phenylpentanoate 
• 128018-43-9 N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 191227-00-6 tert-butyl (4S)-4-N-((S)-tetrahydrofuran-3-yloxycarbonylamino)-5-phenyl-3-oxo-pentanoate 
• 191227-01-7 tert-butyl (4S)-4-N-((S)-tetrahydrofuran-3-yloxycarbonylamino)-2-chloro-5-phenyl-3-oxo-pentanoate 
• 191226-99-0 N-(S)-tetrahydrofuran-3-yloxycarbonyl-L-phenylalanine 
• 111060-52-7 (S)-2-(dibenzylamino)-3-phenylpropan-1-ol 
• 127927-43-9 Dibenzyl-((S)-1-oxiranyl-2-phenyl-ethyl)-amine 
• 191227-02-8 (3S)-1-chloro-2-oxo-3-N-((S)-tetrahydrofuran-3-yloxycarbonylamino)-4-phenylbutane 

Downstream Products

• 160232-13-3 (2R,3S)-3-N-((S)-tetrahydrofuran-3-yloxycarbonylamino)-2-hydroxy-1-N-(isobutyl)amino-4-phenylbutane 
• 160231-69-6 4-nitro-N-((2R(syn),3S)-2-hydroxy-4-phenyl-3-((S)-tetrahydrofuran-3-yloxycarbonylamino)-butyl)-N-isobutylbenzenesulfonamide 

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 preparing oxiranemethanamine derivatives

A process for preparing oxiranemethane derivatives which are useful as intermediates for preparing aspartyl protease inhibitors comprising the steps of activating an aminodiol, acylating the aminodiol and reacting the acylated aminodiol with a base to form an epoxy compound.

Preparation of aminoalkyl chlorohydrin hydrochlorides: Key building blocks for hydroxyethylamine-based HIV protease inhibitors

Enantiomerically pure N,N-dibenzyl-α-amino aldehydes reacted with (chloromethyl)lithium, generated in situ from bromochloromethane and lithium metal, to give predominantly erythro aminoalkyl epoxides. Treatment of the crude epoxides with aqueous hydrochloric acid gave crystalline (2S,3S)-N,N-dibenzylamino chlorohydrin hydrochlorides in 32-56% overall yield and high isomeric purity. These compounds are versatile synthetic intermediates for the preparation of hydroxyethylamine-based HIV protease inhibitors, either directly as such, or via conversion to the corresponding N-Boc(2S,3S)-aminoalkyl epoxides. The processes described do not make use of hazardous reagents or intermediates, do not require chromatographic purifications, and are thus amenable to the preparation of large quantities of these versatile building blocks.