119770-87-5

Upstream product

• 87-91-2 diethyl (2R,3R)-tartrate 
• 100-39-0 benzyl bromide 
• 35572-31-7 (4R,5R)-2-Phenyl-1,3-dioxolan-4,5-dicarbonsaeure-diethylester 
• 104333-85-9 O-benzylidene tartrate 

Downstream Products

• 104211-04-3 L-O-monobenzyl tartaric acid 
• 104211-03-2 (2R,3R)-2-Benzyloxy-3-hydroxy-succinic acid 4-ethyl ester 
• 104225-97-0 (2R,3R)-2-Benzyloxy-3-hydroxy-succinic acid 1-ethyl ester 
• 104211-10-1 [2R-(R*,R*)]-2-hydroxy-3-methoxy-N,N'-bis-(phenylmethoxy)butanediamide 
• 84379-53-3 2-O-benzyl-3,4-O-isopropylidene-L-threitol 
• 131446-96-3 (S)-2-(benzyloxy)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate 
• 99838-63-8 (R)-2-((S)-1-(benzyloxy)propyl)oxirane 
• 108740-35-8 (2S,3S)-3-Benzyloxy-pentane-1,2-diol 
• 334793-69-0 (S)-4-((S)-1-Benzyloxy-propyl)-2,2-dimethyl-[1,3]dioxolane 
• 333788-81-1 (4R,5S)-5-Benzyloxy-hept-1-yn-4-ol 
• 333788-78-6 (2S,3S)-2-Benzyloxy-3-(1-methoxy-1-methyl-ethoxy)-butane-1,4-diol 
• 333788-85-5 (2R,7R)-2-((S)-1-Benzyloxy-propyl)-7-(S)-oxiranyl-2,3,6,7-tetrahydro-oxepine 
• 333788-79-7 (2S,3S)-3-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-pentan-2-ol 
• 333788-69-5 [(R)-1-((S)-1-Benzyloxy-propyl)-but-3-ynyloxy]-tert-butyl-dimethyl-silane 

Relevant academic research and scientific papers

Development of diacyltetrol lipids as activators for the C1 domain of protein kinase C

The protein kinase C (PKC) family of serine/threonine kinases is an attractive drug target for the treatment of cancer and other diseases. Diacylglycerol (DAG), phorbol esters and others act as ligands for the C1 domain of PKC isoforms. Inspection of the crystal structure of the PKCδ C1b subdomain in complex with phorbol-13-O-acetate shows that one carbonyl group and two hydroxyl groups play pivotal roles in recognition of the C1 domain. To understand the importance of two hydroxyl groups of phorbol esters in PKC binding and to develop effective PKC activators, we synthesized DAG like diacyltetrols (DATs) and studied binding affinities with C1b subdomains of PKCδ and PKC. DATs, with the stereochemistry of natural DAGs at the sn-2 position, were synthesized from (+)-diethyl l-tartrate in four to seven steps as single isomers. The calculated EC50 values for the short and long chain DATs varied in the range of 3-6 μM. Furthermore, the fluorescence anisotropy values of the proteins were increased in the presence of DATs in a similar manner to that of DAGs. Molecular docking of DATs (1b-4b) with PKCδ C1b showed that the DATs form hydrogen bonds with the polar residues and backbone of the protein, at the same binding site, as that of DAG and phorbol esters. Our findings reveal that DATs represent an attractive group of C1 domain ligands that can be used as research tools or further structurally modified for potential drug development.

Solvent-free benzylation of polyols by phase-transfer catalysis or supported reagent methods

Solvent-free techniques were successfully and efficiently applied under mild conditions to the perbenzylation of methyl α-D-glucopyranoside and methyl 6-bromo(and 6-chloro)-6-deoxy-α-D-glucopyranoside, and to the selective monobenzylation of diethyl (R,R)

Synthesis of 3α-alkoxy-4β-substituted-2-azetidinones from L(+)-tartaric acid

Tartaric acid, regioselective saponification, Pig Liver Esterase, 3-methoxy-2-azetidinone, N-Hydroxy-2-thiopyridone, radical decarboxylation. The synthesis of 3α-alkoxy-4β-azetidinones from L(+) tartaric acid is described. Regioselective saponification and methylation along with a stereo selective radical decarboxylative alkylation are key steps leading to optically pure trans-β-lactams.

CHIRAL SYNTHESIS OF 3,4-DISUBSTITUTED 2-AZETIDINONES FROM (R,R)-(+)-TARTARIC ACID

A novel route is described for the enantioselective synthesis of 2-azetidinones 24 and 25 from (R,R)-(+)-tartaric acid.Monomethylation, monobenzylation of 2 and the use of site specific pig liver esterase (PLE) to produce 6 and 7 are the key steps in sequ