Benzoyl-l-tartaric acid

Base Information

• Chemical Name: Benzoyl-l-tartaric acid
• CAS No.: 87172-82-5
• Molecular Formula: C11H10O7
• Molecular Weight: 254.196
• DSSTox Substance ID: DTXSID20438280
• Nikkaji Number: J2.896.256H
• Wikidata: Q82253970
• Mol file: 87172-82-5.mol

Synonyms:benzoyl-l-tartaric acid;87172-82-5;SCHEMBL2596611;DTXSID20438280;(2R,3R)-2-(Benzoyloxy)-3-hydroxysuccinic acid;(2R,3R)-2-benzoyloxy-3-hydroxybutanedioic acid

Chemical Property of Benzoyl-l-tartaric acid

Chemical Property:

• PSA: 121.13000
• LogP: -0.25790
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 254.04265265
• Heavy Atom Count: 18
• Complexity: 332

Purity/Quality:

99%+, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)OC(C(C(=O)O)O)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)O[C@H]([C@H](C(=O)O)O)C(=O)O

Technology Process of Benzoyl-l-tartaric acid

There total 6 articles about Benzoyl-l-tartaric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(R,R)-1,2-bis(benzyloxycarbonyl)-2-hydroxyethyl benzoate (158732-35-5) → (2R,3R)-2-(benzoyloxy)-3-hydroxybutanedioic acid (87172-82-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 0.666667h; under 760 Torr; Ambient temperature;

DOI:10.1248/cpb.42.839

Reference yield: 43.0%

L-Tartaric acid (87-69-4,138508-61-9) + benzoyl chloride (98-88-4) → (2R,3R)-2-(benzoyloxy)-3-hydroxybutanedioic acid (87172-82-5) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With sulfuric acid; In 1,2-dimethoxyethane; Reflux;

DOI:10.3998/ark.5550190.0011.b01

Reference yield: 39.0%

L-Tartaric acid (87-69-4,138508-61-9) + benzoyl chloride (98-88-4) → (2R,3R)-2-(benzoyloxy)-3-hydroxybutanedioic acid (87172-82-5) + benzoic acid (65-85-0,8013-63-6) + O,O'-dibenzoyl-L-tartaric acid (2743-38-6)

Guidance literature:

With sulfuric acid; In 1,4-dioxane; at 100 - 102 ℃; for 3h;

DOI:10.3998/ark.5550190.0011.b01

upstream raw materials:

(R,R)-1,2-bis(benzyloxycarbonyl)-2-hydroxyethyl benzoate

L-Tartaric acid

benzoyl chloride

Downstream raw materials:

(2R,3R)-2-Benzoyloxy-3-(6-{(2R,3R)-2-benzoyloxy-3-[5-((1R,2R)-2-benzoyloxy-1,2-bis-benzyloxycarbonyl-ethoxycarbonyl)-pentylcarbamoyl]-3-hydroxy-propionylamino}-hexanoyloxy)-succinic acid dibenzyl ester

O-benzoyl-L-tartaric anhydride

2-methoxyethyl O-benzoyltartrate

C₁₉H₁₅BO₈

Refernces

• 1、 Buschhaus, Boris,Hampel, Frank,Grimme, Stefan,Hirsch, Andreas. "Metal-induced chiral folding of depsipeptide dendrimers". . p. 3530 - 3540. Retrieved 2007/10/03.