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(2S,3S)-2,3-Bis((2-methylbenzoyl)oxy)succinic acid

  • CAS No. 391624-66-1

  • Cat. No. CS-0163122
  • Purity≥98%
  • MDL No.None

*For research and further manufacturing use only, not for direct human use.

(2S,3S)-2,3-Bis((2-methylbenzoyl)oxy)succinic acid|CS-0163122

Structure of 391624-66-1

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General Information

  • CAS No. 391624-66-1
  • Cat. No. CS-0163122
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₀H₁₈O₈
  • Molecular Weight 386.35
  • Synonym(s) Di-o-toluoyl-D-tartaric acid
  • SMILES O=C(O)[C@@H](OC(C1=CC=CC=C1C)=O)[C@H](OC(C2=CC=CC=C2C)=O)C(O)=O

Description

This chiral diester features two (2-methylbenzoyl) ester groups at the 2 and 3 positions of a succinic acid backbone, enabling selective derivatization in asymmetric synthesis. The ortho-methyl substitution enhances steric control during enantioselective transformations.

Application

(2S,3S)-2,3-Bis((2-methylbenzoyl)oxy)succinic acid serves as a chiral auxiliary in asymmetric synthesis, enabling stereocontrolled functionalization through its rigid, well-defined stereocenters. The molecule’s benzoate ester groups provide excellent bench stability and facilitate straightforward purification via crystallization. It functions effectively in diastereoselective transformations, particularly in enantioselective acylations and cyclizations, offering predictable stereochemical outcomes in the construction of complex molecular architectures.

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   127.2
  • LogP   2.22364
  • H_Acceptors   6
  • H_Donors   2
  • Rotatable_Bonds   7

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