38270-72-3

Usage

Uses

Used in Organic Chemistry:
(-)-DIMETHYL 2,3-O-BENZYLIDENE-L-TARTRATE is used as a chiral resolving agent for the separation and purification of enantiomers in organic chemistry. Its ability to distinguish between stereoisomers is essential for the synthesis of chiral compounds with specific biological activities.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (-)-DIMETHYL 2,3-O-BENZYLIDENE-L-TARTRATE is used as a chiral resolving agent to separate and identify stereoisomers. This is crucial for the development of pharmaceutical drugs and other biologically active compounds, as enantiomers can have different effects on the body. By using (-)-DIMETHYL 2,3-O-BENZYLIDENE-L-TARTRATE, researchers can ensure that the desired enantiomer is isolated and used in the final product, leading to more effective and safer medications.

InChI:InChI=1/C13H14O6/c1-16-11(14)9-10(12(15)17-2)19-13(18-9)8-6-4-3-5-7-8/h3-7,9-10,13H,1-2H3/t9-,10-/m1/s1

Upstream product

• 87-69-4 L-Tartaric acid 
• 100-52-7 benzaldehyde 
• 149-73-5 trimethyl orthoformate 
• 608-69-5 dimethyl meso-tartrate 
• 167862-20-6 5-methyl-2-phenyl-1,3-dioxolan-4-one 
• 64714-16-5 2-phenyl-4,5-trans-tetrametylene-1,3-dioxolan 
• 7527-52-8 2-phenyl-1,3-benzodioxole 
• 608-68-4 dimethyl D-(+)-tartrate 
• 608-68-4 dimethyl L-tartrate 
• 1125-88-8 benzaldehyde dimethyl acetal 

Downstream Products

• 114026-73-2 (4R,5R)-α,α,α',α'-2-Pentaphenyl-1,3-dioxolan-4,5-dimethanol 
• 84379-53-3 2-O-benzyl-3,4-O-isopropylidene-L-threitol 
• 130762-71-9 (4R,5R)-α,α,α',α'-tetraphenyl-2-phenyl-1,3-dioxolane-4,5-dimethanol 
• 35572-34-0 (4S,5S)-4,5-dihydroxymethyl-2-phenyldioxolane 
• 84379-51-1 2-O-benzyl-L-threitol 
• 100906-42-1 2-O-benzyl-3,4-O-isopropylidene-L-threose 
• 263550-15-8 (4R,5R)-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid monomethyl ester 
• 79413-91-5 (2S,3S)-2-Benzoyloxy-3-brom-bernsteinsaeuredimethylester 
• 109613-56-1 (2S,3S)-(+)-3-benzyloxy-1,4-bis(tert-butyl-dimethyl-silyloxy)butan-2-ol 
• 109613-57-2 (3R)-(-)-3-benzyloxy-1,4-bis(tert-butyl-dimethyl-silyloxy)butan-2-one 
• 183888-77-9 (2S,3S)-(+)-3-benzyloxy-1,4-bis(tert-butyl-diphenyl-silyloxy)butan-2-ol 
• 183888-69-9 (3R)-3-benzyloxy-1,4-bis(tert-butyl-diphenyl-silyloxy)butan-2-one 
• 599173-62-3 [3-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxymethoxy-propoxymethyl]-benzene 

Relevant academic research and scientific papers

A one-pot synthesis of dimethyl 2,3-O-benzylidene-L-tartrate from L- tartaric acid

An economical one-pot synthesis of (-)-dimethyl 2,3-O-benzylidene-L- tartrate [(4R,5S)-4,5-bis(methoxycarbonyl)-2-phenyl-1,3-dioxolane] and its enantiomer from the corresponding tartaric acids is reported in 83-91% yield. The desired benzylidene tartrate

An Aldehyde Responsive, Cleavable Linker for Glucose Responsive Insulins

A glucose responsive insulin (GRI) that responds to changes in blood glucose concentrations has remained an elusive goal. Here we describe the development of glucose cleavable linkers based on hydrazone and thiazolidine structures. We developed linkers with low levels of spontaneous hydrolysis but increased level of hydrolysis with rising concentrations of glucose, which demonstrated their glucose responsiveness in vitro. Lipidated hydrazones and thiazolidines were conjugated to the LysB29 side-chain of HI by pH-controlled acylations providing GRIs with glucose responsiveness confirmed in vitro for thiazolidines. Clamp studies showed increased glucose infusion at hyperglycemic conditions for one GRI indicative of a true glucose response. The glucose responsive cleavable linker in these GRIs allow changes in glucose levels to drive the release of active insulin from a circulating depot. We have demonstrated an unprecedented, chemically responsive linker concept for biopharmaceuticals.

GLUCOSE-SENSITIVE PEPTIDE HORMONES

The present invention relates to a conjugate of the formula P-L-I, wherein P is a peptide hormone effecting the metabolism of carbohydrates in vivo, L is a hydrolysable linker molecule consisting of Lp and Lj, and I is a molecule capable of inhibiting the effect of the peptide hormone P on the metabolism of carbohydrates in vivo. Under in vivo conditions, the conjugate is the major compound. When the concentration of glucose increases in v/vo,the concentration of the peptide hormone effecting the metabolism of carbohydrates in vivo also increases.

Reaction of (2S,3S)-2-benzyloxybutane-1,2,4-triol with N,N′-carbonyldiimidazole

(2S,3S)-2-Benzyloxybutane-1,2,4-triol reacted with N,N′-carbonyldiimidazole to give a mixture of the expected 1,2-carbonate and the corresponding bis-carbonate.

Total synthesis of pachastrissamine together with its 4-epi-congener via [3,3]-sigmatropic rearrangements and antiproliferative/cytotoxic evaluation Dedicated to Associated Professor Ladislav Knie?o on the occasion of his 70th birthday

Synthesis of the HCl salts of two anhydrophytosphingosines, jaspine B (1) and its 4-epi-congener 5 from easily available dimethyl l-tartrate and/or l-arabinose, is described. The key transformations are the efficient incorporation of a chiral amino group

Total synthesis of pachastrissamine together with its 4-epi-congener via [3,3]-sigmatropic rearrangements and antiproliferative/cytotoxic evaluation Dedicated to Associated Professor Ladislav Knieo on the occasion of his 70th birthday

Synthesis of the HCl salts of two anhydrophytosphingosines, jaspine B (1) and its 4-epi-congener 5 from easily available dimethyl l-tartrate and/or l-arabinose, is described. The key transformations are the efficient incorporation of a chiral amino group

Facile synthesis of (2R,3S)-2-benzyloxy-3-hydroxybutyrolactone

The heterocyclic diols derived from L-dimethyl tartrate are important chiral synthons in organic synthesis. In particular, L-threosolactone and L-threosolactam structures are versatile precursors for the synthesis of biologically active molecules. Structu

Modification of chiral dimethyl tartrate through transesterification: Immobilization on POSS and enantioselectivity reversal in sharpless asymmetric epoxidation

Modification of dimethyl tartrate has been investigated through transesterification with aminoalcohols to provide reactive functionalities for the covalent bonding of chiral tartrate to polyhedral oligomeric silsesquioxanes. The transesterification of dimethyl tartrate has been widely studied using different catalytic systems and reaction conditions. Through the proper selection of both the catalytic system and the reaction conditions, it is possible to achieve monosubstituted or bis-substituted tartrate derivatives as sole products. All the intermediate chiral tartrate-derived ligands were successfully used in the homogeneous enantioselective epoxidation of allylic alcohols providing moderate enantiomeric excess over the products. Attached amine groups have been used to support the modified tartrate ligands on to a haloaryl-functionalized silsesquioxane moiety. This final chiral tartrate ligand displays reverse enantioselectivity in the asymmetric epoxidation of allylic alcohols with regard to the starting dimethyl tartrate ligand, both molecules having the same chiral sign. However, the POSS-containing ligand can be easily recovered in almost quantitative yield and reused in asymmetric epoxidation reactions. In addition, recovered silsesquioxane-pendant ligand, though displaying decreasing catalytic activity in recycling epoxidation tests, showed very stable enantioselective behavior.

Design and evaluation of inclusion resolutions, based on readily available host compounds

Resolution of enantiomers through selective crystallisation of diastereomeric inclusion compounds can extend the scope of traditional racemate resolution beyond salt forming compounds. To assess the practical value of this approach the literature was carefully screened and promising results were checked. Also an extensive range of new inclusion hosts suitable for resolution processes, derived from simple hydroxy- and amino acids were prepared and tested. Several techniques, including the Dutch Resolution approach utilizing mixtures of resolving agents, were applied. Over 70 potential resolving agents were tested in combinations with 34 racemates (over 100 racemates if literature results are included). Reproducibility of literature results was found to be problematic. Also the number of successful new resolutions found was very limited: only two efficient resolutions out of 1200 combinations of racemate and resolving agent tested in over 10.000 experiments! Crystal studies of representative combinations of resolving agents and inclusion compounds revealed some of the causes for the low rate of success in inclusion resolution. Compared to diastereomeric salts, the absence of strong electrostatic interactions substantially reduces the probability of forming crystals including both components. Molecular structure features allowing formation of intricate intramolecular and intermolecular H-bond networks were found to be responsible for inclusion crystal formation, and for the quality of the ensuing resolution through selective diastereomer crystallisation, in the successful cases. Whereas diastereomeric salt resolution continues to be of scientific and industrial interest, inclusion resolution should be viewed as of very limited scope; useful in specific instances, but lacking the wide applicability of classical resolution. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Studies of intramolecular alkylidene carbene reactions; an approach to heterocyclic nucleoside bases

A series of investigations into the applications of intramolecular cyclisations of alkylidene carbenes are described. The insertion reaction of the carbene generated from 1,4-di(tert-butyldimethylsilyloxy)-3-benzyloxy-butane-2-one to the benzylic position