119770-87-5

Basic information

• Product Name: diethyl (2S,3S)-2-(benzyloxy)-3-hydroxybutanedioate
• Synonyms: diethyl (2S,3S)-2-(benzyloxy)-3-hydroxybutanedioate
• CAS NO: 119770-87-5
• Molecular Weight: 296.32
• Mol File: 119770-87-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: diethyl (2S,3S)-2-(benzyloxy)-3-hydroxybutanedioate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl (2S,3S)-2-(benzyloxy)-3-hydroxybutanedioate(119770-87-5)
• EPA Substance Registry System: diethyl (2S,3S)-2-(benzyloxy)-3-hydroxybutanedioate(119770-87-5)

Safety Data

• Hazardous Substances Data: 119770-87-5(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 333788-77-5 (2R,3R)-2-Benzyloxy-3-(1-methoxy-1-methyl-ethoxy)-succinic acid diethyl ester 
• 84379-52-2 (2R,3R)-3-(benzyloxy)butane-1,2,4-triol 
• 92206-12-7 (2S,3S)-2,4-bis(benzyloxy)butane-1,3-diol 
• 114185-00-1 1,2-di-O-benzyl-L-threitol 
• 84379-51-1 2-O-benzyl-L-threitol 
• 1395045-12-1 (2S,3S)-1,3-bis(benzyloxy)-4-(octanoyloxy)butan-2-yl octanoate 
• 1395045-10-9 (2S,3S)-1,3-bis(benzyloxy)-4-(hexadecanoyloxy)butan-2-yl hexadecanoate 
• 1351168-21-2 tert-butyl 4-((3S,4S)-4-(benzyloxy)-3-(2-fluoro-4-(methylsulfonyl)phenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate 
• 1351168-20-1 tert-butyl 4-((3S,4S)-4-(benzyloxy)-3-(4-bromo-2-fluorophenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate 
• 1351168-19-8 tert-butyl 4-((3R,4S)-4-(benzyloxy)-3-(methylsulfonyloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate 
• 1351168-18-7 tert-butyl 4-((3R,4S)-4-(benzyloxy)-3-hydroxy-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate 
• 1351168-17-6 (R)-2-(benzyloxy)-2-((R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetaldehyde 
• 1351168-16-5 (R)-S-ethyl 2-(benzyloxy)-2-((R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)ethanethioate 
• 1351168-85-8 (R)-2-(benzyloxy)-2-((R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid 

Relevant articles and documents

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.

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.