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(1S,2R)-2-(Benzyloxymethyl)-1-hydroxy-3-cyclopentene

  • CAS No. 110567-21-0

  • Cat. No. CS-W005682
  • Purity≥95%
  • MDL No.MFCD09263486

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

(1S,2R)-2-(Benzyloxymethyl)-1-hydroxy-3-cyclopentene|CS-W005682

Structure of 110567-21-0

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General Information

  • CAS No. 110567-21-0
  • Cat. No. CS-W005682
  • Purity ≥95%
  • MDL No. MFCD09263486
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₆O₂
  • Molecular Weight 204.27
  • Synonym(s) Entecavir inter-7
  • SMILES C(C1=CC=CC=C1)OC[C@H]2C=CC[C@@H]2O

Description

This chiral cyclopentene derivative features a hydroxyl group at C1 and a benzyloxymethyl substituent at C2, enabling selective functionalization in asymmetric synthesis. The rigid cyclopentene core provides defined stereochemistry, while the benzyloxy handle offers orthogonal protection. Stable under standard bench conditions, this intermediate facilitates efficient access to complex carbocyclic architectures.

Application

(1S,2R)-2-(Benzyloxymethyl)-1-hydroxy-3-cyclopentene serves as a versatile chiral building block in synthetic organic chemistry, enabling stereoselective transformations via its functionalized cyclopentene core. The pendant benzyloxymethyl group provides a robust, bench-stable protecting group for the hydroxyl functionality, facilitating selective derivatization and orthogonal handling in complex molecule synthesis. Its defined stereochemistry supports reliable asymmetric synthesis workflows, particularly in natural product and pharmaceutical intermediate development.

Synthesis

  • Route1
    • In-stock
      Benzyl chloromethyl ether|CS-0015122
      3587-60-8
    • null|null
      4984-82-1
    • ~72%
    • In-stock
      (1S,2R)-2-(Benzyloxymethyl)-1-hydroxy-3-cyclopentene|CS-W005682
      110567-21-0

    References

    • Woll, Matthew G.; Fisk, John D.; LePlae, Paul R.; Gellman, Samuel H. Journal of the American Chemical Society, 2002 , vol. 124, # 42 p. 12447 - 12452
  • Route2
    • ((Cyclopenta-2,4-dien-1-ylmethoxy)methyl)benzene|CS-1089778
      39939-07-6
    • ~%
    • In-stock
      (1S,2R)-2-(Benzyloxymethyl)-1-hydroxy-3-cyclopentene|CS-W005682
      110567-21-0

    References

    • Biggadike, Keith; Borthwick, Alan D.; Evans, Derek; Exall, Anne M.; Kirk, Barrie E.; et al. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988 , p. 549 - 554
  • Route3

    References

    • Synthesis, , # 13 p. 2101 - 2109

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

Quality Control

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Computational Chemistry Data

  • TPSA   29.46
  • LogP   2.1402
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   4

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