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CS-W001157 4
Total: USD 88.00

(S)-Dimethyl 2-hydroxysuccinate

  • CAS No. 617-55-0

  • Cat. No. CS-W007994
  • Purity≥97%
  • MDL No.MFCD00066215

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

(S)-Dimethyl 2-hydroxysuccinate|CS-W007994

Structure of 617-55-0

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General Information

  • CAS No. 617-55-0
  • Cat. No. CS-W007994
  • Purity ≥97%
  • MDL No. MFCD00066215
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₁₀O₅
  • Molecular Weight 162.14
  • Synonym(s) L-(-)-Malic Acid Dimethyl Ester
  • SMILES C([C@@H](O)CC(=O)OC)(=O)OC

Description

Dimethyl (S)-(-)-malate may be used as a starting material to synthesize (-)-tulipalin B. The selective reduction of its ester group to alcohol can be accomplished using borane-dimethyl sulfide complex (BMS) in the presence of sodium tetrahydroborate.

Application

(S)-Dimethyl 2-hydroxysuccinate serves as a stereochemically defined building block for asymmetric synthesis, enabling the construction of chiral diacid derivatives and heterocyclic scaffolds. Its hydroxyl and ester functionalities offer orthogonal reactivity for selective transformations, including derivatization, protection, or metal-catalyzed coupling reactions. The compound exhibits good bench stability and facilitates purification via standard chromatographic methods, making it well-suited for iterative synthetic sequences in medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • Nagano, Masanobu; Tanaka, Masakazu; Doi, Mitsunobu; Demizu, Yosuke; Kurihara, Masaaki; Suemune, Hiroshi Organic Letters, 2009 , vol. 11, # 5 p. 1135 - 1137
  • Route2
    • In-stock
      (S)-Malic acid|CS-W020132
      97-67-6
    • null|null
      149-73-5
    • ~97%
    • In-stock
      (S)-Dimethyl 2-hydroxysuccinate|CS-W007994
      617-55-0

    References

    • Zurwerra, Didier; Glaus, Florian; Betschart, Leo; Schuster, Julia; Gertsch, Juerg; Ganci, Walter; Altmann, Karl-Heinz Chemistry - A European Journal, 2012 , vol. 18, # 52 p. 16868 - 16883
  • Route3
    • null|null
      67-56-1
    • null|null
      201230-82-2
    • null|null
      4538-50-5
    • ~92%
    • In-stock
      (S)-Dimethyl 2-hydroxysuccinate|CS-W007994
      617-55-0

    References

    • Hinterding, Klaus; Jacobsen, Eric N. Journal of Organic Chemistry, 1999 , vol. 64, # 7 p. 2164 - 2165

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS02,GHS05,GHS07
Signal Word : Danger
UN#: 1993
Class : 3
Packing Group : Ⅲ
Hazard Statements : H226-H317-H318
Precautionary Statements : P210-P233-P240-P241-P242-P243-P261-P272-P280-P302+P352-P362+P364-P370+P378-P501

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Computational Chemistry Data

  • TPSA   72.83
  • LogP   -0.9166
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   3

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