146953-71-1

Upstream product

• 63-91-2 L-phenylalanine 
• 20312-36-1 L-3-phenyllactic acid 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 7622-21-1 benzyl-(S)-(-)-2-hydroxy-3-phenylpropionate 

Downstream Products

• 319921-46-5 (R,R)-2-{4-[1-(Phenylmethyloxycarbonyl)ethylamino]-1H-indol-3-yl}-1-(hydroxymethyl)ethylphenylacetamide 
• 934482-04-9 (1S,2S,4R,5S)-4-((R)-1-benzyloxycarbonyl-2-phenyl-ethoxy)-5-hydroxy-cyclohexane-1,2-dicarboxylic acid dimethyl ester 
• 1403603-68-8 (2R)-2-{(2S,3R,4S,5S,6R)-2-[(2R,3R)-1,4-dimethoxy-1,4-dioxo-3-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)butan-2-yloxy]-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy}-3-phenylpropanoic acid 
• 1403603-70-2 (R)-benzyl-2-((2R,3S,4S,5R,6S)-2-(benzyloxymethyl)-6-(ethylthio)-3-hydroxy-5-(4-methoxybenzyloxy)tetrahydro-2H-pyran-4-yloxy)-3-phenylpropanoate 
• 1403603-72-4 (2R,3S,4S,5R,6S)-4-((R)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-yloxy)-5(benzyloxycarbonyloxy)-2-(benzyloxymethyl)-6-(ethylthio)tetrahydro-2H-pyran-3-yl 1-naphtoate 
• 1403603-71-3 (2R,3S,4S,5R,6S)-4-((R)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-yloxy)-5-(benzyloxycarbonyloxy)-2-(benzyloxymethyl)-6-(ethylthio)tetrahydro-2H-pyran-3-yl benzoate 
• 1403603-81-5 (2R,3S,4R,5R,6S)-4-((R)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-yloxy)-2-(benzyloxymethyl)-6-(ethylthio)-5-hydroxytetrhydro-2H-pyran-3-yl benzoate 
• 1403603-80-4 (2R,3S,4S,5R,6S)-4-((R)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-yloxy)-2-(benzyloxymethyl)-6-(ethylthio)-5-(4-methoxybenzyloxy)tetrahydro-2H-pyran-yl benzoate 
• 866890-44-0 methyl {2,4,6-tri-O-acetyl-3-O-[(R)-1-(benzyloxycarbonyl)-2-phenylethyl]-β-D-galactopyranosyl}-(1->3)-2-(acetylamino)-4,6-di-O-acetyl-2-deoxy-β-D-galactopyranoside 
• 866890-39-3 methyl {2-O-acetyl-4,6-O-benzylidene-3-O-[(R)-1-(benzyloxycarbonyl)-2-phenylethyl]-β-D-galactopyranosyl}-(1->3)-2-(acetylamino)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 
• 866890-52-0 (R)-2-[(2R,3R,4S,5S,6R)-2-((2R,3R,4R,5R,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-3-phenyl-propionic acid benzyl ester 
• 934482-18-5 (1S,2S,4S,5R)-4-((R)-1-benzyloxycarbonyl-2-phenyl-ethoxy)-5-(2-acetamido-4,6-O-dipivaloyl-3-O-acetyl-2-deoxy-β-D-galactopyranosyl)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester 

Relevant academic research and scientific papers

A new approach to explore the binding space of polysaccharide-based ligands: Selectin antagonists

The discovery of molecules that interfere with the binding of a ligand to a receptor remains a topic of great interest in medicinal chemistry. Herein, we report that a monosaccharide unit of a polysaccharide ligand can be replaced advantageously by a conformationally locked acyclic molecular entity. A cyclic component of the selectin ligand Sialyl Lewisx, GlcNAc, is replaced by an acyclic tether, tartaric esters, which link two saccharide units. The conformational bias of this acyclic tether originates from the minimization of intramolecular dipole-dipole interaction and the gauche effect. The evaluation of the binding of these derivatives to P-selectin was measured by surface plasmon resonance spectroscopy. The results obtained in our pilot study suggest that the discovery of tunable tethers could facilitate the exploration of the carbohydrate recognition domain of various receptors.

A simple model system for the study of carbohydrate-aromatic interactions

A molecular scaffold was identified which enables the establishment of intramolecular interactions between a monosaccharide and a nearby phenyl ring. A group of molecules containing four different monosaccharides (glucose, galactose, N-acetyl-glucosamine,

Intramolecular carbohydrate-aromatic interaction and intermolecular van der Waals interactions enhance the molecular recognition ability of GM1 glycomimetics for cholera toxin

The design and synthesis of two GM1 glycomimetics, 6 and 7, and analysis of their conformation in the free state and when complexed to cholera toxin is described. These compounds, which include an (R)-cyclohexyllactic acid and an (R)-phenyllactic acid fra

Solid-phase synthesis and biological evaluation of a teleocidin library - Discovery of a selective PKCδ down regulator

Protein kinase C (PKC) is linked to the signal-induced modulation of a wide variety of cellular processes, such as growth, differentiation, secretion, apoptosis, and tumor development. The design and synthesis of small molecules that regulate these different cellular signaling systems is at the forefront of modern drug design. Herein we report a) an efficient method for the synthesis of indolactam V (6), a PKC activator, and its N13-des(methyl) analogues (19) using a regioselective organometallic transformation, a convenient aminomalonate derivative (10) to introduce the appropriate functionality and an enantiospecific enzymic hydrolysis as key steps; b) the use of this method in the first solid-phase synthesis of a teleocidin library modifying the N-13, C-12 and C-7 alkyl chains, and, therefore, producing a library of potential activators and/or inhibitors of PKC of the general structure (32); c) the activation of PKC by selected members of the library using a MARCKS translocation in vivo assay system; d) the observation that some of these analogues are nearly as effective as the natural PKC activators phorbol dibutyrate and (-)-indolactam V (6), and e) the observation that some of these analogues have different potential to induce down-regulation of members of the PKC gene family after chronic stimulation.

Synthesis of (15)N-Labelled Chiral Boc-Amino Acids from Triflates: Enantiomers of Leucine and Phenylalanine

An efficient synthesis of (15)N-labelled chiral Boc-amino acids by triflate alkylation of di-tert-butyl iminodicarbonate is reported.Both enantiomers of Boc-Leucine and -phenylalanine were synthesized from commercial α-amino acids of opposite configuration via α-hydroxy carboxylic acids provided by diazotization, thus extending the scope of an earlier exploratory study.The high chiral purity of the final products was confirmed by HPLC.These labelled amino acid derivatives are suitable for direct application to the synthesis of labelled peptides.