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CS-W001157 4
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(4S,5R)-4-Hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one

  • CAS No. 34371-14-7

  • Cat. No. CS-0053170
  • Purity≥97%
  • MDL No.None

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

(4S,5R)-4-Hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one|CS-0053170

Structure of 34371-14-7

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General Information

  • CAS No. 34371-14-7
  • Cat. No. CS-0053170
  • Purity ≥97%
  • MDL No. None
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₈O₄
  • Molecular Weight 132.11
  • Synonym(s) (4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one (non-preferred name)
  • SMILES OC[C@H]1OC(=O)C[C@@H]1O

Description

This dihydrofuranone scaffold features a stereochemically defined hydroxyl and hydroxymethyl group, enabling precise integration into complex natural product syntheses. The rigid cyclic structure enhances stability under standard reaction conditions, while the functionalized side chain supports selective derivatization in synthetic workflows.

Application

(4S,5R)-4-Hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one serves as a stereochemically defined building block for the synthesis of bioactive heterocycles and carbohydrate analogs. Its constrained dihydrofuran core enables predictable regioselective transformations, while the adjacent hydroxyl and hydroxymethyl groups offer orthogonal functionalization sites. The compound exhibits excellent bench stability and facilitates efficient derivatization in standard organic workflows, making it valuable for medicinal chemistry and natural product synthesis.

Synthesis

  • Route1
    • null|null
      91879-31-1
    • ~93%
    • In-stock
      (4S,5R)-4-Hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one|CS-0053170
      34371-14-7

    References

    • Miranda, Pedro O.; Estevez, Francisco; Quintana, Jose; Garcia, Candelaria I.; Brouard, Ignacio; Padron, Juan I.; Pivel, Juan P.; Bermejo, Jaime Journal of Medicinal Chemistry, 2004 , vol. 47, # 2 p. 292 - 295
  • Route2

    References

    • Scarpi, Dina; Bartali, Laura; Casini, Andrea; Occhiato, Ernesto G. European Journal of Organic Chemistry, 2013 , # 7 p. 1306 - 1317
  • Route3
    • null|null
      83159-90-4
    • ~86%
    • In-stock
      (4S,5R)-4-Hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one|CS-0053170
      34371-14-7

    References

    • Kozikowski,, Alan P.; Ghosh, Arun K. Journal of Organic Chemistry, 1984 , vol. 49, # 15 p. 2762 - 2772

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   66.76
  • LogP   -1.3449
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   1

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