76498-22-1

Usage

InChI:InChI=1/C18H19NO5/c20-16(17(21)22)15(11-13-7-3-1-4-8-13)19-18(23)24-12-14-9-5-2-6-10-14/h1-10,15-16,20H,11-12H2,(H,19,23)(H,21,22)/t15-,16+/m1/s1

Upstream product

• 151-50-8 potassium cyanide 
• 501-53-1 benzyl chloroformate 
• 62023-23-8 [(R)-1-Benzyl-2-(3,5-dimethyl-pyrazol-1-yl)-2-oxo-ethyl]-carbamic acid benzyl ester 
• 247178-59-2 methyl (2S,3R)-3-(benzyloxycarbonyl)amino-2-formyloxy-4-phenylbutanoate 
• 591-51-5 phenyllithium 
• 95832-30-7 N-<(benzyloxy)carbonyl>-(2R)-amino-1-phenylbut-3-ene 
• 95891-28-4 (4R,5S)-3,4-Dibenzyl-5-hydroxymethyl-oxazolidin-2-one 
• 95832-31-8 Z-D-phenylalanine ethyl ester 
• 95832-34-1 Benzyl-((R)-1-benzyl-allyl)-carbamic acid benzyl ester 
• 95832-35-2 (4R,5S)-3,4-Dibenzyl-5-iodomethyl-oxazolidin-2-one 
• 200616-24-6 (3S)-N-(benzyloxycarbonyl)-3-amino-4-phenylbutane-1,2-diol 
• 150767-05-8 (S)-2-(phenylmethoxycarbonyl)amino-1-phenylbut-3-ene 
• 62023-57-8 (S)-1-(2'-benzyloxycarbonylamino-3'-phenylpropanoyl)-3,5-dimethylpyrazole 
• 62023-62-5 allophenylnorstatine 

Downstream Products

• 60016-66-2 benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl]-L-leucinate 
• 62058-27-9 Z-(2S,3R)-AHPA-(R)-Leu-OBzl 
• 62058-28-0 Z-(2S,3S)-AHPA-(S)-Leu-OBzl 
• 62058-29-1 Z-(2S,3S)-AHPA-(R)-Leu-OBzl 
• 62023-09-0 N-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]glycine 

Relevant academic research and scientific papers

Multifunctional immunity-targeted micromolecule anti-cancer medicine (Bestazomib citrate) and preparation method and application thereof

The invention discloses multifunctional immunity-targeted micromolecule anti-cancer medicine (Bestazomib citrate) and a preparation method and application thereof. A structure of the multifunctional immunity-targeted micromolecule anti-cancer medicine (Be

Chemoselective catalytic oxidation of 1,2-diols to α-hydroxy acids controlled by TEMPO-ClO2 charge-transfer complex

Chemoselective catalytic oxidation from 1,2-diols to α-hydroxy acids in a cat. TEMPO/cat. NaOCl/NaClO2 system has been achieved. The use of a two-phase condition consisting of hydrophobic toluene and water suppresses the concomitant oxidative cleavage. A study of the mechanism suggests that the observed selectivity is derived from the precise solubility control of diols and hydroxy acids as well as the active species of TEMPO. Although the oxoammonium species TEMPO+Cl- is hydrophilic, the active species dissolves into the organic layer by the formation of the charge-transfer (CT) complex TEMPO-ClO2 under the reaction conditions.

HIV protease inhibitors

Combinatorial libraries of HIV and FIV protease inhibitors are characterized by alpha-keto amide or hydroxyethylamine core structures flanked by on one side by substituted pyrrolidines, piperidines, or azasugars and on the other side by phenylalanine, tyrosine, or substituted tyrosines. The libraries are synthesized via a one step coupling reaction. Highly efficacious drug candidates are identified by screening the libraries for binding and inhibitory activity against both HIV and FIV protease. Drug candidates displaying clinically useful activity against both HIV and FIV protease are identified as being potentially resistive against a loss of inhibitory activity due to development of resistant strains of HIV.

Novel synthesis of (-)-bestatin from L-aspartic acid

Oxazoline-4-acetate derivative 3 that could be readily obtained from L-aspartic acid was subjected to highly stereoselective hydroxylation, and subsequent Mitsunobu inversion of the hydroxyl group led to (2S,3R)-3-amino-3-benzyl-2-hydroxybutanoic acid der

Development of a new type of protease inhibitors, efficacious against FIV and HIV variants

Based on the structural analysis of FIV protease and drug-resistant HIV proteases and molecular modeling, a new type of inhibitors with a small P3 residue has been developed. These inhibitors are effective against HIV and its drug-resistant mutants, as well as SIV and FIV. Modification of existing HIV protease inhibitors by reducing the size of the P3 residue has the same effect. This finding provides a new strategy for the development of HIV protease inhibitors effective against the wild-type and drug-resistant mutants. It further supports the use of FIV protease as a useful model for drug-resistant HIV proteases, which often have a more constricted binding region for the P3 group or the combined P3 and P1 groups.

Ring opening of optically active cis-disubstituted aziridino alcohols: An enantiodivergent synthesis of functionalized amino alcohol derivatives

Ring-opening reactions of optically active cis-disubstituted aziridino alcohols have been investigated. Regio- and stereo-selective ring opening took place with internal and external nucleophiles. Unusual amino acids derivatives (14) and (15), the key synthetic intermediates for bestatin and related peptides, have been prepared. n.

Selectivity in the inhibition of HIV and FIV protease: Inhibitory and mechanistic studies of pyrrolidine-containing α-keto amide and hydroxyethylamine core structures

This paper describes the development of new pyrrolidine-containing α-keto amide and hydroxyethylamine core structures as mechanism based inhibitors of the HIV and FIV proteases. It was found that the α-keto amide core structure 2 is approximately 300-fold better than the corresponding hydroxyethylamine isosteric structure and 1300-fold better than the corresponding phosphinic acid derivative as an inhibitor of the HIV protease. The α-keto amide is however not hydrated until it is bound to the HIV protease as indicated by the NMR study and the X-ray structural analysis. Further analysis of the inhibition activities of hydroxyethylamine isosteres containing modified pyrrolidine derivatives revealed that a cis-methoxy group at C-4 of the pyrrolidine would improve the binding 5- and 25-fold for the trans-isomer. When this strategy was applied to the α-keto amide isostere, a cis-benzyl ether at C-4 was found to enhance binding 3-fold. Of the core structures prepared as inhibitors of the HIV protease, none show significant inhibitory activity against the mechanistically identical FIV protease, and additional complementary groups are needed to improve inhibition.

An enantiodivergent synthesis of three β-amino alcohols: Preparation of key intermediates for bestatin and the related peptides

An enantiodivergent method for preparation of three β-amino alcohols and three 1,2-diamines has been developed starting with a chiral aziridine 1. Unusual amino acid derivatives 3 and 5, which are key synthetic intermediates for bestatin and the related peptides, have been prepared.

Diastereoselective process for the preparation of intermediates useful for the synthesis of peptide derivatives

A diastereoselective process for the preparation of compounds of formula STR1 (wherein R and R1 have the meanings reported in the specification and the asterisks show the asymmetric carbon atoms) starting from the corresponding N-protected 2-am