43457
(−)-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
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
2008171
Assay:
≥98.0% (T)
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
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-HTQZYQBOSA-N
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
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
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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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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