(+)-Dimethyl 2,3-O-benzylidene-D-tartrate

Base Information

• Chemical Name: (+)-Dimethyl 2,3-O-benzylidene-D-tartrate
• CAS No.: 91326-83-9
• Molecular Formula: C13H14 O6
• Molecular Weight: 266.251
• DSSTox Substance ID: DTXSID10352123
• Nikkaji Number: J461.068G
• Mol file: 91326-83-9.mol

Synonyms:(+)-Dimethyl 2,3-O-benzylidene-D-tartrate;91326-83-9;Dimethyl (4S,5S)-2-phenyl-1,3-dioxolane-4,5-dicarboxylate;Dimethyl 2,3-O-benzylidene-D-tartrate;SCHEMBL20712075;DTXSID10352123;(4S,5S)-2-Phenyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester;(4S,5S)-dimethyl 2-phenyl-1,3-dioxolane-4,5-dicarboxylate;(+)-Dimethyl 2,3-O-benzylidene-D-tartrate, >=98.0% (sum of enantiomers, GC)

Chemical Property of (+)-Dimethyl 2,3-O-benzylidene-D-tartrate

Chemical Property:

• Vapor Pressure: 1.96E-07mmHg at 25°C
• Melting Point: 74-76 °C(lit.)
• Refractive Index: 1.546
• Boiling Point: 409.3°C at 760 mmHg
• Flash Point: 158.7°C
• PSA: 71.06000
• Density: 1.364g/cm³
• LogP: 0.81520
• Storage Temp.: 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 266.07903816
• Heavy Atom Count: 19
• Complexity: 312

Purity/Quality:

98%min ^*data from raw suppliers

(+)-Dimethyl 2,3-O-benzylidene-D-tartrate ≥98.0% (sum of enantiomers, GC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1C(OC(O1)C2=CC=CC=C2)C(=O)OC
• Isomeric SMILES: COC(=O)[C@@H]1[C@H](OC(O1)C2=CC=CC=C2)C(=O)OC

Technology Process of (+)-Dimethyl 2,3-O-benzylidene-D-tartrate

There total 12 articles about (+)-Dimethyl 2,3-O-benzylidene-D-tartrate 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: 91.0%

dimethyl L-tartrate (608-68-4) + benzaldehyde (100-52-7) → 4,5-trans-bis(methoxycarbonyl)-2-phenyl-1,3-dioxolan (38270-70-1,38270-71-2,38270-72-3,91326-83-9,117306-81-7,129519-91-1)

Guidance literature:

toluene-4-sulfonic acid; In benzene; Heating;

DOI:10.1016/S0040-4039(00)89235-7

Reference yield: 88.0%

D-tartaric acid (147-71-7,138508-61-9) + benzaldehyde (100-52-7) + trimethyl orthoformate (149-73-5) → (4S,5S)-dimethyl 2-phenyl-1,3-dioxolane-4,5-dicarboxylate (91326-83-9)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 0.166667h; Ambient temperature;

DOI:10.1080/00397919308011180

Reference yield: 67.0%

Dimethyl D-tartrate (13171-64-7) + benzaldehyde dimethyl acetal (1125-88-8) → (4S,5S)-dimethyl 2-phenyl-1,3-dioxolane-4,5-dicarboxylate (91326-83-9)

Guidance literature:

With toluene-4-sulfonic acid; In cyclohexane; for 6h; Reflux;

DOI:10.1016/j.tetlet.2013.07.164

upstream raw materials:

dimethyl L-tartrate

benzaldehyde

dimethyl D-(+)-tartrate

2-phenyl-1,3-benzodioxole

Downstream raw materials:

2-O-benzyl-L-threitol

benzaldehyde

dimethyl D-(+)-tartrate monobenzoate

<2-chloro-1,2-bis(methoxycarbonyl)>ethyl benzoate