99113-33-4

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 152683-75-5 ((1S,2R)-1-Benzyl-2-hydroxy-3-oxo-propyl)-carbamic acid tert-butyl ester 
• 68709-71-7 tert-butyl 4-bromo-3-oxo-1-phenylbutan-2-ylcarbamate 
• 213603-02-2 (1S,2S)-(E)-4-[N-(tert-butyloxycarbonyl)amino]-1,5-diphenylpent-1-en-3-ol 
• 213603-00-0 (4S,5S)-4-Benzyl-5-((E)-styryl)-oxazolidin-2-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 152359-60-9 ethyl (E)-(5S)-6-phenyl-5-[(tert-butyloxycarbonyl)amino]-4-oxo-2-hexenoate 

Downstream Products

• 135103-86-5 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-hexanoic acid ethyl ester 
• 133333-27-4 tert-butyl (1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate 
• 126409-25-4 (2R,4S,5S)-N,2-dibenzyl-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenylhexanamide 

Relevant academic research and scientific papers

Transition-state mimetics for HIV protease inhibitors: Stereocontrolled synthesis of hydroxyethylene and hydroxyethylamine isosteres by ester- derived titanium enolate syn and anti-aldol reactions

Stereocontrolled syntheses of hydroxyethylene dipeptide isostere and aminoalkyl epoxides for hydroxyethylamine isosteres are described. The stereochemistry of both stereogenic centers of the aminoalkyl epoxides 10 and 15 as well as they γ-lactone 17 was assembled by our recently developed highly selective ester-derived titanium enolate aldol reactions. The Ti- enolate of 6 reacted with (benzyloxy)acetaldehyde and cinnamaldehyde to provide the syn-aldol product 7 and anti-aldol product 12, respectively. Removal of the chiral template followed by Curtius rearrangement of the resulting acid provided the desired amine functionality. The present syntheses represent practical and enantioselective entry to a range of other dipeptide isosteres, which are not limited to amino acid derived substituents.

Peptide inhibitors of aspartic proteinases with hydroxyethylene isostere replacement of peptide bond. I. Preparation of four diastereoisomeric (2R or 2S, 4R or 4S, 5S)-2-benzyl-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenylhexanoic acids

By two separate routes were prepared four diastereoisomers of (2R or 2S,5R or 5S)-3-benzyl-5-{(1S)-[(tert-butoxycarbonyl)amino]-2-phenylethyl}tetrahydrofuran- 2-ones (11, 12, 17 and 18). Since the furanones were derived from (S)-phenylalanine, absolute co