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43456

Sigma-Aldrich

(+)-O,O′-Di-pivaloyl-D-tartaric acid

≥98.0%

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Synonym(s):
(+)-DPTA
Linear Formula:
[(CH3)3CCO2CH(CO2H)-]2
CAS Number:
76769-55-6
Molecular Weight:
318.32
Beilstein:
6894779
MDL number:
MFCD00015634
UNSPSC Code:
12352108
eCl@ss:
39021705
PubChem Substance ID:
57650180
NACRES:
NA.22

Quality Level

100

Assay

≥98.0%

optical activity

[α]20/D +23.5±1°, c = 1.7% in dioxane

mp

127-130 °C (lit.)

SMILES string

CC(C)(C)C(=O)O[C@@H]([C@H](OC(=O)C(C)(C)C)C(O)=O)C(O)=O

InChI

1S/C14H22O8/c1-13(2,3)11(19)21-7(9(15)16)8(10(17)18)22-12(20)14(4,5)6/h7-8H,1-6H3,(H,15,16)(H,17,18)/t7-,8-/m0/s1

InChI key

UFHJEZDFEHUYCR-YUMQZZPRSA-N

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General description

(+)-O,O′-Di-pivaloyl-D-tartaric acid is a chiral protonating agent (CPA).

Other Notes

Reagent for the "deracemization" of carbonyl compounds by enantio-selective protonation of enamines or Li-enolates ; Synthesis of optically active α-amino acids

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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Enantioselective protonations: fundamental insights and new concepts.
Duhamel L, et al.
Tetrahedron Asymmetry, 15(23) (2004)
Deracemisation par protonation enantioselective.
L. Duhamel, J.-C. Plaquevent
Tetrahedron Letters, 2285-2285 (1977)
Ligand exchange in asymmetric reactions of lithium enolates: application to the deracemization of a-aminoacids.
L. Duhamel et al.
Tetrahedron Letters, 27, 4975-4975 (1986)
L. Duhamel
Bulletin de la Societe Chimique De France, II, 421-421 (1984)
Deracemization by enantioselective protonation. A new method for the enantiomeric enrichment of. alpha.-amino acids.
L. Duhamel, J.-C. Plaquevent
Journal of the American Chemical Society, 100, 7415-7415 (1978)

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