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CAS 156835-63-1

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O,O′-Di-p-toluoyl-D-tartaric anhydride

Description:
O,O′-Di-p-toluoyl-D-tartaric anhydride is a chemical compound that belongs to the class of tartaric acid derivatives. It is characterized by the presence of two p-toluoyl groups attached to the anhydride form of D-tartaric acid, which contributes to its unique reactivity and properties. This compound is typically used as a chiral auxiliary in asymmetric synthesis, facilitating the formation of enantiomerically enriched products. Its structure includes a bicyclic anhydride moiety, which enhances its electrophilic character, making it suitable for various chemical transformations. The presence of the p-toluoyl groups also influences its solubility and stability in organic solvents. Additionally, O,O′-Di-p-toluoyl-D-tartaric anhydride can participate in reactions with nucleophiles, leading to the formation of new chiral centers. Overall, this compound is valued in synthetic organic chemistry for its ability to promote stereoselective reactions, making it a useful tool in the development of pharmaceuticals and other fine chemicals.
Formula:C20H16O7
InChI:InChI=1S/C20H16O7/c1-11-3-7-13(8-4-11)17(21)25-15-16(20(24)27-19(15)23)26-18(22)14-9-5-12(2)6-10-14/h3-10,15-16H,1-2H3/t15-,16-/m0/s1
InChI key:InChIKey=BCIJHROJBLWCLV-HOTGVXAUSA-N
SMILES:O(C(=O)C1=CC=C(C)C=C1)[C@H]2[C@H](OC(=O)C3=CC=C(C)C=C3)C(=O)OC2=O
Synonyms:
  • Benzoic acid, 4-methyl-, (3S,4S)-tetrahydro-2,5-dioxo-3,4-furandiyl ester
  • Benzoic acid, 4-methyl-, tetrahydro-2,5-dioxo-3,4-furandiyl ester, (3S-trans)-
  • O,O′-Di(p-toluoyl)-D-tartaric acid anhydride
  • O,O′-Di-p-toluoyl-D-tartaric anhydride
  • Benzoic acid, 4-methyl-, 1,1′-[(3S,4S)-tetrahydro-2,5-dioxo-3,4-furandiyl] ester
  • DI-P-TOLUOYL-D-TARTARIC ANHYDRIDE
  • [(3S,4S)-4-(4-methylbenzoyl)oxy-2,5-dioxooxolan-3-yl] 4-methylbenzoate
  • (3S,4S)-2,5-dioxotetrahydrofuran-3,4-diyl bis(4-methylbenzoate)
  • D-PTAN
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