622-00-4

Basic information

• Product Name: L-TARTARIC ACID DIBENZYL ESTER
• Synonyms: Dibenzyl L-Tartrate;Di Benzyl-L-Tartarate;(+)-DIBENZYL-L-TARTRATE;DIBENZYL L-TARTRATE;L-TARTARIC AIC DIBENZYL ESTER;L-TARTARIC ACID DIBENZYL ESTER;L-DBT;L-(+)-Dibenzyl Tartrate
• CAS NO: 622-00-4
• Molecular Formula: C₁₈H₁₈O₆
• Molecular Weight: 330.33
• Product Categories: Chiral Building Blocks;Esters (Chiral);Synthetic Organic Chemistry;Asymmetric Synthesis;Chiral Catalysts, Ligands, and Reagents;EpoxidationChiral Building Blocks;Esters;Organic Building Blocks
• Mol File: 622-00-4.mol
• Article Data: 19

Chemical Properties

• Melting Point: 51-54 °C
• Boiling Point: 427.78°C (rough estimate)
• Flash Point: 171.5°C
• Appearance: /
• Density: 1.2036
• Vapor Pressure: 4.64E-10mmHg at 25°C
• Refractive Index: -13 ° (C=1, Acetone)
• PKA: 11.38±0.20(Predicted)
• BRN: 3221733
• CAS DataBase Reference: L-TARTARIC ACID DIBENZYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: L-TARTARIC ACID DIBENZYL ESTER(622-00-4)
• EPA Substance Registry System: L-TARTARIC ACID DIBENZYL ESTER(622-00-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 622-00-4(Hazardous Substances Data)

Usage

General Description

L-Tartaric acid dibenzyl ester is a chemical compound that is derived from tartaric acid. It is commonly used as a reagent in organic synthesis, particularly in the asymmetric synthesis of organic compounds. It is a clear, colorless liquid with a faint, fruity odor. L-Tartaric acid dibenzyl ester is often used as a chiral auxiliary in the synthesis of pharmaceuticals and other organic compounds, as it can help to control the stereochemistry of the reaction. L-TARTARIC ACID DIBENZYL ESTER is considered to be relatively safe when handled and used properly, but it may cause irritation to the skin and eyes, and should be handled with care.

InChI:InChI=1/C18H18O6/c19-15(17(21)23-11-13-7-3-1-4-8-13)16(20)18(22)24-12-14-9-5-2-6-10-14/h1-10,15-16,19-20H,11-12H2/t15-,16-/m1/s1

Upstream product

• 87-69-4 L-Tartaric acid 
• 100-51-6 benzyl alcohol 
• 97-72-3 2-Methylpropionic anhydride 
• 5005-35-6 2-pyridyl benzoate 
• 622-00-4 dibenzyl (+)-tartrate 
• 100-39-0 benzyl bromide 
• 52709-42-9 benzylglyoxylate 
• 643028-20-0 dibenzyl (4R,5R)-1,3,2-dioxathiolane-4,5-dicarboxylate 2-oxide 

Downstream Products

• 103710-70-9 Dibenzyl (2R,3R)-2-O-Benzyltartrate 
• 152714-46-0 benzyl (2R,3R)-3-hydroxy-2-<(2,6-diisopropoxybenzoyl)oxy>-butanedioate 
• 119197-63-6 (R,R)-O-tert-butyl-dibenzyl tartrate 
• 119197-64-7 (R,R)-O,O-di-tert-butyl-dibenzyl tartrate 
• 87-92-3 (+)-(2R,3R)-dibutyl tartrate 
• 158732-36-6 benzyl (2R,3R)-3-hydroxy-2-<(2,6-dimethoxybenzoyl)-oxy>butanedioate 
• 26549-65-5 N,N,N',N'-tetramethyl L-tartramide 
• 488148-82-9 dibenzyl (-)-(2R,3R)-2,3-bis{3-[2,3-bis(3,4-dibenzyloxy)phenyl]prop-2-enoyloxy}-L-tartrate 
• 64056-73-1 Benzyl α-(Triphenylphosphoranylidene)-α-{5-(tert-butoxycarbonyl)-4-[2'-(methoxycarbonyl)ethyl]-3-methylpyrrol-2-yl}acetate 
• 135145-04-9 5-Benzyloxyoxalyl-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester 
• 135145-02-7 Benzyl α-Hydroxy-α-(5-(tert-butoxycarbonyl)-4-(2'-(methoxycarbonyl)ethyl)-3-methylpyrrol-2-yl)acetate 
• 64091-58-3 5-{Benzyloxycarbonyl-[3-eth-(E)-ylidene-4-methyl-5-oxo-pyrrolidin-(2Z)-ylidene]-methyl}-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester 
• 1257665-38-5 (R,R)-dibenzyl tartrate mono-3,5-di(tert-butyl)benzoate 
• 1448779-05-2 C₂₇H₂₄O₉ 

Relevant articles and documents

Selective Monoacylation of Diols and Asymmetric Desymmetrization of Dialkyl meso-Tartrates Using 2-Pyridyl Esters as Acylating Agents and Metal Carboxylates as Catalysts

With 2-pyridyl benzoates as acylating agents and Zn(OAc)2 as a catalyst, 1,2-diols, 1,3-diols, and catechol were selectively monoacylated. Furthermore, the highly enantioselective desymmetrization of meso-tartrates was achieved for the first time, utilizing 2-pyridyl esters and NiBr2/AgOPiv/Ph-BOX in CH3CN or CuCl2/AgOPiv/Ph-BOX in EtOAc catalyst systems (up to 96% ee). The latter catalyst system was also effective for the kinetic resolution of dibenzyl dl-tartrate.

Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts

An extremely efficient acylative kinetic resolution of d,l-1,2-diols in the presence of only 0.5 mol% of binaphthyl-based chiral N,N-4-dimethylaminopyridine was developed (selectivity factor of up to 180). Several key experiments revealed that hydrogen bonding between the tert-alcohol unit(s) of the catalyst and the 1,2-diol unit of the substrate is critical for accelerating the rate of monoacylation and achieving high enantioselectivity. This catalytic system can be applied to a wide range of substrates involving racemic acyclic and cyclic 1,2-diols with high selectivity factors. The kinetic resolution of d,l-hydrobenzoin and trans-1,2-cyclohexanediol on a multigram scale (10 g) also proceeded with high selectivity and under moderate reaction conditions: (i) very low catalyst loading (0.1 mol%); (ii) an easily achievable low reaction temperature (0 °C); (iii) high substrate concentration (1.0 M); and (iv) short reaction time (30 min). (Figure presented.).

The catalytic synthesis of carboniolamide: The role of sp 3 hybridized oxygen

A catalytic synthesis of carboniolamide has been reported. The strategy was straightforward with aldehyde and amide as starting materials. The products can be isolated as precipitates from the reaction mixture. The factor that stabilizes the labile functionality of hemiaminal was elucidated as a sp 3 hybridized oxygen.