43456
(+)-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:
Molecular Weight:
318.32
NACRES:
NA.22
PubChem Substance ID:
eCl@ss:
39021705
UNSPSC Code:
12352108
MDL number:
Beilstein/REAXYS Number:
6894779
Assay:
≥98.0%
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
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 key
UFHJEZDFEHUYCR-YUMQZZPRSA-N
assay
≥98.0%
optical activity
[α]20/D +23.5±1°, c = 1.7% in dioxane
mp
127-130 °C (lit.)
functional group
carboxylic acid, ester
Quality Level
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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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)
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)
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