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(3S,4R,5S)-Methyl 3,4,5,6-tetrahydroxy-2-oxohexanoate

  • CAS No. 3031-98-9

  • Cat. No. CS-0150930
  • Molecule weight208.17
  • Purity≥95%
  • MDL No.MFCD00021987

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

(3S,4R,5S)-Methyl 3,4,5,6-tetrahydroxy-2-oxohexanoate|CS-0150930

Structure of 3031-98-9

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General Information

  • CAS No. 3031-98-9
  • Cat. No. CS-0150930
  • Purity ≥95%
  • MDL No. MFCD00021987
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₂O₇
  • Molecular Weight 208.17
  • Synonym(s) Methyl 2-keto-L-gulonate
  • SMILES COC(=O)C(=O)[C@H]([C@@H]([C@H](CO)O)O)O

Description

This tetrahydroxylated oxohexanoate ester features a stereochemically defined core with hydroxyl groups at C3, C4, C5, and C6, enabling precise engagement in glycosylation reactions. The methyl ester facilitates handling and integration into complex carbohydrate synthesis workflows.

Application

(3S,4R,5S)-Methyl 3,4,5,6-tetrahydroxy-2-oxohexanoate serves as a key chiral building block for the synthesis of complex carbohydrate derivatives and natural product scaffolds. Its defined stereochemistry enables stereoselective glycosylation reactions and facilitates access to polyhydroxylated heterocycles. The molecule exhibits good bench stability and is compatible with standard protecting group strategies, making it suitable for multi-step synthetic sequences in medicinal chemistry and carbohydrate chemistry applications.

Synthesis

  • Route1
    • (3S,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxohexanoic acid Ascorbic Acid Impurity|CS-0533277
      526-98-7
    • ~%
    • In-stock
      (3S,4R,5S)-Methyl 3,4,5,6-tetrahydroxy-2-oxohexanoate|CS-0150930
      3031-98-9

    References

    • ARCHER-DANIELS-MIDLAND COMPANY Patent: EP1206435 B1, 2004 ; Location in patent: Page column 8-9 ;
  • Route2
    • null|null
      67-56-1
    • (3S,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxohexanoic acid Ascorbic Acid Impurity|CS-0533277
      526-98-7
    • ~%
    • In-stock
      (3S,4R,5S)-Methyl 3,4,5,6-tetrahydroxy-2-oxohexanoate|CS-0150930
      3031-98-9

    References

    • Drefahl; Gross Journal fuer Praktische Chemie (Leipzig), 1955 , vol. <4> 1, p. 153,154
  • Route3
    • Vitamin C solution|CS-1692914
      50-81-7
    • ~1%
    • In-stock
      (3S,4R,5S)-Methyl 3,4,5,6-tetrahydroxy-2-oxohexanoate|CS-0150930
      3031-98-9

    References

    • Rhone Poulenc Rorer S.A. Patent: US5391770 A1, 1995 ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H317-H319
Precautionary Statements : P261-P264-P272-P280-P302+P352-P362+P364-P501

Quality Control

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Computational Chemistry Data

  • TPSA   124.29
  • LogP   -3.1965
  • H_Acceptors   7
  • H_Donors   4
  • Rotatable_Bonds   5

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