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371416

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/REAXYS Number:
2022481
EC Number:
MDL number:
UNSPSC Code:
12352106
eCl@ss:
39021705
PubChem Substance ID:
NACRES:
NA.22

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

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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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