143601-45-0

Upstream product

• 540-88-5 acetic acid tert-butyl ester 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 100-41-4 ethylbenzene 
• 501-53-1 benzyl chloroformate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 1161-13-3 N-Cbz-L-Phe 
• 1207973-75-8 lithium tert-butyl acetate 

Downstream Products

• 198020-19-8 (2R,2S)-(3S)-1,2-epoxy-3-phenylmethoxycarbonylamino-4-phenylbutane 
• 19317-12-5 (3S)-3-(N-benzyloxycarbonylamino)-3-benzyl-2-oxo-1-bromopropane 
• 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 
• 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 
• 160232-67-7 (2S,3S)-3-Amino-1-chloro-4-phenyl-butan-2-ol 
• 183255-96-1 (2R,3S)-1-chloro-2-hydroxy-3-N-benzyloxycarbonylamino-4-phenylbutane 
• 128018-43-9 N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol 
• 26049-94-5 (S)-benzyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate 
• 191226-90-1 tert-butyl (4S)-4-N-benzyloxycarbonylamino-2-chloro-3-oxo-5-phenylpentanoate 
• 191226-91-2 4-benzyloxycarbonylamino-2-bromo-3-oxo-5-phenyl-pentanoic acid tert-butyl ester 
• 143601-50-7 phenylmethyl [(1S)-2-phenyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]ethyl]carbamate 
• 143601-46-1 (S)-5-Benzyloxycarbonylamino-4-oxo-6-phenyl-hexanoic acid ethyl ester 

Relevant academic research and scientific papers

A SIMPLE SYNTHETIC APPROACH TO Cbz-Phe-Ψ-(CH2)Gly-Pro-OMe AND RELATED PEPTIDE ISOSTERES

A new approach to ketomethylene and hydroxymethylene peptide isosteres has been developed which is simple, direct, and highly convergent.A key feature is construction of the central bond of a γ-keto ester by alkylation of a t-butyl β-keto ester with an α-bromo ester.

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.

An efficient synthesis of γ-amino β-ketoester by cross-Claisen condensation with α-amino acid derivatives

Cross-ester condensation between N-protected amino acid ester and the lithium enolate prepared from alkyl acetate gave the corresponding β-ketoester in high yield without the formation of the tertiary alcohol that is commonly seen as by-product. This inte

Synthesis of optically active α-aminoalkyl α′-halomethyl ketone: A cross-claisen condensation approach

(Equation presented) A simple and versatile method was developed for the synthesis of α-aminoalkyl α′-halomethyl ketone derivatives, which are useful intermediates of protease inhibitors. It involves selective halogenation of the α-position on a β-ketoester, which is prepared by cross-Claisen condensation using N-protected amino acid ester. The title compound is obtained in high yield after decarboxylation of the α-halo-β-ketoester.

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.

A simple, stereoselective synthesis of ketomethylene dipeptide isosteres

An exceedingly simple, general, and stereoselective method for the preparation of ketomethylene dipeptide isosteres (5-(carbobenzyloxyamino)-2-alkyl-γ-ketoesers) from Cbz-protected amino acids and scalemic-2-triflyloxy esters has been developed. The method is short (three steps), efficient, and highly diastereoselective and enantioselective.