133333-27-4

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 137038-63-2 deux références: JFP452-1 et JFP456b 
• 207222-78-4 (S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-phenyl-hexanoic acid ethyl ester 
• 172329-54-3 Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-6-phenylhexanoate 
• 210294-29-4 [(S)-1-((S)-5-Oxo-2,5-dihydro-furan-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 135103-86-5 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-hexanoic acid ethyl ester 
• 742109-02-0 (4S,5S)-4-Benzyl-5-(2-ethoxycarbonyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 54966-42-6 ethyl 3-benzylacrylate 
• 134458-64-3 (4S,5S)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-benzyl-5-formyl-1,3-oxazolidine 
• 139163-87-4 (2R,3S)-methyl 3-amino-2-hydroxy-4-phenylbutanoate 
• 116565-10-7 (2R,3S)-N-(tert-butoxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester 
• 203806-77-3 (4S,5R)-4-Benzyl-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester 
• 742109-00-8 ethyl (2R,3S)-3-acetylamino-2-hydroxy-4-phenylbutanoate 
• 99113-33-4 (E)-(4S,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-phenyl-hex-2-enoic acid ethyl ester 

Downstream Products

• 160431-24-3 5(S)-[1(S)-(Boc-amino)-2-phenyl-ethyl]-3(R)-(p-methoxy-phenylmethyl)-dihydrofuran-2-(3H)-one 
• 165453-99-6 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-(2,3,4-trimethoxyphenylmethyl)-dihydrofuran-2-(3H)-one 
• 98818-41-8 (3R,5S)-3-benzyl-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}dihydrofuran-2-(3H)-one 
• 178049-11-1 5(S)-[1(S)-(Boc-Amino)-2-phenylethyl]-3(R)-[(2,4-dimethoxyphenyl)methyl]-dihydrofuran-2-(3H)-one 
• 137281-77-7 {(1S)-1-[(4R)-4-allyl-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester 
• 212790-57-3 {(S)-1-[(2S,4R)-4-(3-Methyl-butyl)-5-oxo-tetrahydro-furan-2-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester 
• 212790-59-5 {(S)-1-[(2S,4S)-4-(1-Hydroxy-cyclohexyl)-5-oxo-tetrahydro-furan-2-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester 
• 98818-42-9 (3S,5S)-3-benzyl-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}dihydrofuran-2-(3H)-one 
• 165453-53-2 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-[(2,4-difluorophenyl)methyl]-dihydro-furan-2-(3H)-one 
• 126410-43-3 (3R,5S,1'S)-3-(4-benzyloxyphenylmethyl)-5-(1((1,1-dimethylethoxycarbonyl)amino)-2-phenylethyl)-dihydrofuran-2-(3H)-one 

Relevant academic research and scientific papers

A formal stereoselective synthesis of a hydroxyethylene dipeptide isostere

4-Hydroxy-5-amino-6-phenyl-4-hexanolide has been synthesized under its cyclized form (lactone 5) from a very inexpensive chiral starting material, L-glutamic acid. The key steps were an original reduction of carbonyl of a ketone with n-Bu3SnH i

Application of the asymmetric aminohydroxylation reaction for the syntheses of HIV-protease inhibitor, hydroxyethylene dipeptide isostere and γ-amino acid derivative

An enantioselective synthesis of lactone 1, a precursor to the (2R,4S,5S) hydroxyethylene dipeptide isostere and amino acid AHPPA 2 has been accomplished from the common intermediate 5 employing Sharpless asymmetric aminohydroxylation as the key step.

Ring-closing metathesis strategy to unsaturated γ- and δ-lactones: Synthesis of hydroxyethylene isostere for protease inhibitors

Ring-closing olefin metathesis of acrylates derived from allylic and homo allylic alcohols in the presence of the Grubbs' catalyst (10-15 mol%) and titanium isopropoxide (0.3-3 equiv) provided ready access to α, β- unsaturated γ and δ-lactones and an important dipeptide isostere intermediate.

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

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.

Use of compositions for combating tumour diseases

The present invention relates to the use of inhibitors of HIV aspartate proteases, such as HIV-1- or HIV-2-protease, and their salts and to prodrugs for inhibiting the growth of tumors, especially those tumors which do not respond to the inhibition of HIV

Thiazole-Based Stereoselective Routes to Leucine and Phenylalanine Hydroxyethylene Dipeptide Isostere Inhibitors of Renin and HIV-1 Aspartic Protease

A new synthesis of hydroxyethylene dipeptide isosteres for Leu-Leu and Phe-Phe in their γ-lactone form 1a and 1b employing β-amino-α-hydroxy aldehydes with singly and doubly protected nitrogen has been developed.These key intermediates, which are availabl

Process for the preparation of a substituted diaminoalcohol

A process is disclosed for the preparation of a substituted diaminoalcohol of the formula: STR1

Diastereoselective Synthesis of the Key Lactone Intermediate for the Preparation of Hydroxyethylene Dipeptide Isosteres

An efficient and highly stereoselective route for preparing hydroxyethylene dipeptide isosteres from α-N,N-dibenzylamino ketones has been developed.

Stereoselective Synthesis of a Hydroxyethylene Dipeptide Isostere

A stereoselective synthesis of a hydroxyethylene dipeptide isostere for Phe-Gly, (4S, 5S)-4-hydroxy-5-amino-6-phenylhexanoic acid, is described.The use of dibenzyl protecting groups on ketoamine 5 accounts for the selectivity on reduction.Also, the dibenzyl group plays a role in directing the introduction of a third chiral center.