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Sigma-Aldrich

(−)-O,O′-Di-p-toluoyl-L-tartaric acid

97%

Synonym(s):

L-(-)-DTTA, Di-p-toluyl-L-tartaric acid

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About This Item

Linear Formula:
[CH3C6H4CO2CH(CO2H)-]2
CAS Number:
Molecular Weight:
386.35
Beilstein:
2022481
EC Number:
MDL number:
UNSPSC Code:
12352106
eCl@ss:
39021705
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

powder

optical activity

[α]20/D −138°, c = 1 in ethanol

mp

169-171 °C (lit.)

SMILES string

Cc1ccc(cc1)C(=O)O[C@H]([C@@H](OC(=O)c2ccc(C)cc2)C(O)=O)C(O)=O

InChI

1S/C20H18O8/c1-11-3-7-13(8-4-11)19(25)27-15(17(21)22)16(18(23)24)28-20(26)14-9-5-12(2)6-10-14/h3-10,15-16H,1-2H3,(H,21,22)(H,23,24)/t15-,16-/m1/s1

InChI key

CMIBUZBMZCBCAT-HZPDHXFCSA-N

General description

(-)-O,O′-Di-p-toluoyl-L-tartaric acid is a O,O′-diacyl tartaric acid derivative that can be prepared by the resolution of its racemate in the presence of cinchonine.

Application

(-)-O,O′-Di-p-toluoyl-L-tartaric acid may be used as a chiral resolving agent for the resolution of the racemic bases to isolate the (-)-enantiomeric forms.
Resolving agent for racemic amines.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tetrahedron Letters, 32, 7325-7325 (1991)
Synthetic Communications, 20, 3553-3553 (1990)
Highly efficient resolution of (?)-Tramadol with di-p-toluoyl-tartaric acid (DTTA).
Evans GR, et al.
Tetrahedron Asymmetry, 12(11) null

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