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43457

Sigma-Aldrich

(−)-O,O′-Di-pivaloyl-L-tartaric acid

≥98.0% (T)

Synonym(s):

(−)-DPTA

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About This Item

Empirical Formula (Hill Notation):
C14H22O8
CAS Number:
Molecular Weight:
318.32
Beilstein:
2008171
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22

Assay

≥98.0% (T)

optical activity

[α]20/D −23.5±1°, c = 1.7% in dioxane

mp

127-132 °C

functional group

carboxylic acid
ester

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-/m1/s1

InChI key

UFHJEZDFEHUYCR-HTQZYQBOSA-N

Application

(−)-O,O′-Di-pivaloyl-L-tartaric acid can be used:
  • As a chiral staple in the synthesis of helical π-conjugated cyclic nanocoils, which are used as nano springs, nano solenoids, and pressure sensors.[1]
  • As an additive in the iridium-catalyzed C-H amidation reactions of arylphosphoryl compounds.[2]

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

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Dual role of carboxylic acid additive: mechanistic studies and implication for the asymmetric C--H amidation
Gwon D, et al.
Tetrahedron, 71(26-27), 4504-4511 (2015)
Versatile Bottom-up Approach to Stapled π-Conjugated Helical Scaffolds: Synthesis and Chiroptical Properties of Cyclic o-Phenylene Ethynylene Oligomers
Fuentes N, et al.
Angewandte Chemie (International Edition in English), 124(52), 13213-13217 (2012)

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