174603-02-2

Upstream product

• 53585-93-6 (R)-(-)-hexahydromandelic acid 
• 100-39-0 benzyl bromide 
• 716362-15-1 benzyl 2-cyclohexyl-2-hydroxyethanoate 
• 117-34-0 2,2-diphenylacetic acid 
• 1760-46-9 diphenylacetic anhydride 
• 14328-52-0 (R)-2-amino-2-cyclohexyl acetic acid 

Downstream Products

• 187403-13-0 benzyl (R)-2-cyclohexyl-2-(trifluoromethylsulfonyloxy)acetate 
• 866890-31-5 methyl {4,6-O-benzylidene-3-O-[(S)-(benzyloxycarbonyl)(cyclohexyl)methyl]-β-D-galactopyranosyl}-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 
• 866890-41-7 methyl {2,4,6-tri-O-acetyl-3-O-[(S)-(benzyloxycarbonyl)(cyclohexyl)methyl]-β-D-galactopyranosyl}-(1->3)-2-(acetylamino)-4,6-di-O-acetyl-2-deoxy-β-D-galactopyranoside 
• 866890-36-0 methyl {2-O-acetyl-4,6-O-benzylidene-3-O-[(S)-1-(benzyloxycarbonyl)(cyclohexyl)methyl]-β-D-galactopyranosyl}-(1->3)-2-(acetylamino)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 
• 182205-74-9 C₇₄H₁₁₀N₈O₁₄ 
• 182205-73-8 C₇₄H₁₁₀N₈O₁₄ 
• 182205-71-6 (S)-3-Hydroxy-3-methyl-2-methylamino-butyric acid (R)-[((S)-1-benzyloxycarbonyl-2-methyl-propyl)-methyl-carbamoyl]-cyclohexyl-methyl ester 
• 182269-67-6 (R)-3-Hydroxy-3-methyl-2-methylamino-butyric acid (R)-[((S)-1-benzyloxycarbonyl-2-methyl-propyl)-methyl-carbamoyl]-cyclohexyl-methyl ester 

Relevant academic research and scientific papers

Selective Monovalent Galectin-8 Ligands Based on 3-Lactoylgalactoside

Galectin-8 has gained attention as a potential new pharmacological target for the treatment of various diseases, including cancer, inflammation, and disorders associated with bone mass reduction. To that end, new molecular probes are needed in order to better understand its role and its functions. Herein we aimed to improve the affinity and target selectivity of a recently published galectin-8 ligand, 3-O-[1-carboxyethyl]-β-d-galactopyranoside, by introducing modifications at positions 1 and 3 of the galactose. Affinity data measured by fluorescence polarization show that the most potent compound reached a KD of 12 μM. Furthermore, reasonable selectivity versus other galectins was achieved, making the highlighted compound a promising lead for the development of new selective and potent ligands for galectin-8 as molecular probes to examine the protein's role in cell-based and in vivo studies.

METHOD FOR PRODUCING OPTICALLY ACTIVE 2-HYDROXY ESTER AND NOVEL INTERMEDIATE COMPOUND

Disclosed is a method for producing an optically active 2-hydroxy ester, comprising selectively esterifying one enantiomer of a racemic 2-hydroxy ester in a solvent containing a catalyst such as tetramisole or benzotetramisole, and a carboxylic acid anhydride, or a carboxylic acid anhydride and a carboxylic acid. In particular, in the case where the solvent contains a carboxylic acid anhydride, but does not contain a carboxylic acid, as the carboxylic acid anhydride, a carboxylic acid anhydride containing a tertiary or quaternary carbon atom in the a-position is used. On the other hand, in the case where the solvent contains a carboxylic acid anhydride and a carboxylic acid, as the carboxylic acid, a carboxylic acid containing a tertiary or quaternary carbon atom in the a-position is used.

A convenient method for the kinetic resolution of racemic 2-hydroxyalkanoates using diphenylacetic anhydride (DPHAA) and a chiral acyl-transfer catalyst

Diphenylacetic anhydride (DPHAA) was found to be a useful reagent for the kinetic resolution of racemic 2-hydroxyalkanoates in the presence of a catalytic amount of (R)-benzotetramisole ((R)-BTM). The combined use of DPHAA and (R)-BTM effectively produced a variety of the optically active 2-hydroxyalkanoates and the corresponding 2-acyloxyalkanoates from racemic 2-hydroxyalkanoates (s-values = 42-177). A fairly broad substrate scope was demonstrated by this novel chiral induction system. We also revealed that the use of only 0.3 equiv of DPHAA is enough to provide the optically active 2-acyloxyalkanoates in good yields and with excellent ee's by the added use of 0.3 equiv of pivalic anhydride for the kinetic resolution of the racemic 2-hydroxyalkanoates. Copyright

Kinetic resolution of the racemic 2-hydroxyalkanoates using the enantioselective mixed-anhydride method with pivalic anhydride and a chiral acyl-transfer catalyst

A variety of optically active 2-hydroxyalkanoates and the corresponding 2-acyloxyalkanoates are produced by the kinetic resolution of racemic 2-hydroxyalkanoates by using achiral 2,2-diarylacetic acid with hindered carboxylic anhydrides as the coupling reagents. The combined use of diphenylacetic acid, pivalic anhydride, and (+)-(R)-benzotetramisole ((R)-BTM) effectively produces (S)-2-hydroxyalkanoates and (R)-2-acyloxyalkanoates from the racemic 2-hydroxyalkanoates (s-values = 47-202). This protocol directly provides the desired chiral 2-hydroxyalkanoate derivatives from achiral diarylacetic acid and racemic secondary alcohols that do not include the sec-phenethyl alcohol moiety by using the transacylation process to generate the mixed anhydrides from the acid components with bulky carboxylic anhydrides under the influence of the chiral acyl-transfer catalyst. The transition state that provides the desired (R)-2-acyloxyalkanoate from (R)-2-hydroxyalkanoate included in the racemic mixture is disclosed by DFT calculations, and the structural features of the transition form are also discussed.

Synthesis of ganglioside mimics for binding studies with myelin-associated glycoprotein (MAG)

Glycosylation of 3-O-unprotected 2-azido-2-deoxy-galactopyranoside (compound 5) with O-(2,3-di-O-acyl-4,6-O-benzylidene-D-galactopyranosyl) trichloroacetimidates (compounds 4A, B) as glycosyl donors afforded β(1-3)-linked disaccharides (9A, B) in high yie

1,3,4-Trisubstituted pyrrolidine CCR5 receptor antagonists. Part 4: Synthesis of N-1 acidic functionality affording analogues with enhanced antiviral activity against HIV

A series of α-(pyrrolidin-1-yl)acetic acids is presented as selective and potent antivirals against HIV. Several of the pyrrolidine zwitterions demonstrated reasonable in vitro properties, enhanced antiviral activities and improved pharmacokinetic profiles over pyrrolidine 1.