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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

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.
  • As an additive in the iridium-catalyzed C-H amidation reactions of arylphosphoryl compounds.

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

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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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)
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)

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