133333-27-4Relevant academic research and scientific papers
A formal stereoselective synthesis of a hydroxyethylene dipeptide isostere
Peyrat, Jean-Francois
, p. 2757 - 2760 (1995)
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
Kondekar, Nagendra B.,Kandula, Subba Rao V.,Kumar, Pradeep
, p. 5477 - 5479 (2007/10/03)
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.
Transition-state mimetics for HIV protease inhibitors: Stereocontrolled synthesis of hydroxyethylene and hydroxyethylamine isosteres by ester- derived titanium enolate syn and anti-aldol reactions
Ghosh,Fidanze
, p. 6146 - 6152 (2007/10/03)
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.
Ring-closing metathesis strategy to unsaturated γ- and δ-lactones: Synthesis of hydroxyethylene isostere for protease inhibitors
Ghosh, Arun K.,Cappiello, John,Shin, Dongwoo
, p. 4651 - 4654 (2007/10/03)
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
Litera, Jaroslav,Budesinsky, Milos,Urban, Jan,Soucek, Milan
, p. 231 - 244 (2007/10/03)
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
Use of compositions for combating tumour diseases
-
, (2008/06/13)
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
Process for the preparation of a substituted diaminoalcohol
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, (2008/06/13)
A process is disclosed for the preparation of a substituted diaminoalcohol of the formula: STR1
Thiazole-Based Stereoselective Routes to Leucine and Phenylalanine Hydroxyethylene Dipeptide Isostere Inhibitors of Renin and HIV-1 Aspartic Protease
Dondoni, Alessandro,Perrone, Daniela,Semola, M. Teresa
, p. 7927 - 7933 (2007/10/03)
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
Diastereoselective Synthesis of the Key Lactone Intermediate for the Preparation of Hydroxyethylene Dipeptide Isosteres
Lagu, Bharat R.,Liotta, Dennis C.
, p. 547 - 550 (2007/10/02)
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
Diederich, Ann M.,Ryckman, David M.
, p. 6169 - 6172 (2007/10/02)
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.
