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43456

Sigma-Aldrich

(+)-O,O′-Di-pivaloyl-D-tartaric acid

≥98.0%

Synonym(s):

(+)-DPTA

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About This Item

Linear Formula:
[(CH3)3CCO2CH(CO2H)-]2
CAS Number:
76769-55-6
Molecular Weight:
318.32
Beilstein/REAXYS Number:
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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Related Categories

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

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)

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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Deracemisation par protonation enantioselective.
L. Duhamel, J.-C. Plaquevent
Tetrahedron Letters, 2285-2285 (1977)
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)
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)
Enantioselective protonations: fundamental insights and new concepts.
Duhamel L, et al.
Tetrahedron Asymmetry, 15(23) (2004)

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