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

Downstream Products

• 608-68-4 dimethyl L-tartrate 
• 87-91-2 diethyl (2R,3R)-tartrate 
• 130678-34-1 Dibenzyl-(4R,5R)-2-<(RS)-4,8-dimethylnonyl>-2-methyl-1,3-dioxolan-4,5-dicarboxylat 
• 103710-70-9 Dibenzyl (2R,3R)-2-O-Benzyltartrate 
• 152714-46-0 benzyl (2R,3R)-3-hydroxy-2-<(2,6-diisopropoxybenzoyl)oxy>-butanedioate 
• 128971-82-4 (4R,5R)-Dibenzyl 1,3,2-Dioxathiolane-4,5-dicarboxylate 2,2-Dioxide 
• 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 
• 158732-35-5 (R,R)-1,2-bis(benzyloxycarbonyl)-2-hydroxyethyl benzoate 
• 127349-17-1 (R,R)-(-)-O,O'-dibenzoyltartaric acid N,N,N',N'-tetramethyldiamide 
• 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 

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.

New pH-responsive gemini lipid derived co-liposomes for efficacious doxorubicin delivery to drug resistant cancer cells

A gemini version of the amphiphile palmitoyl homocysteine was synthesized. Co-liposomes were prepared using the gemini along with a natural zwitterionic lipid, DOPE and cholesterol at specified ratios. This afforded pH-responsive co-liposomes which could efficiently transport the anticancer drug, doxorubicin (DOX), across the DOX-resistant HeLa cancer cells in response to low pH of cellular endosomes.

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.