A bicyclic γ-lactone
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(−)-G-Lactone

Item No. 30488

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,3aR,6,6aS-tetrahydro-2H-cyclopenta[b]furan-2-one
CAS Number
43119-28-4
Molecular Formula
C7H8O2
Formula Weight
124.1
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:2): 0.33 mg/mlEthanol: 15 mg/ml
SMILES
O=C1C[C@@]2([H])[C@@](CC=C2)([H])O1
InChi Code
InChI=1S/C7H8O2/c8-7-4-5-2-1-3-6(5)9-7/h1-2,5-6H,3-4H2/t5-,6-/m0/s1
InChi Key
RYBPGUMSFWGGLP-WDSKDSINSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    250 mg

    $75

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    500 mg

    $134

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    1 g

    $238

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    5 g

    $736

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    Product Description

    (–)-G-lactone is a bicyclic γ-lactone prostaglandin chiral synthon and a building block.1,2 It is a prostaglandin chiral synthon formed from an asymmetric Baeyer-Villiger oxidation reaction.1 (–)-G-lactone has also been used as a building block in the synthesis of HIV-1 protease inhibitors.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Alphand, V., Archelas, A., and Furstoss, R. Microbial Transformations 16. One-step synthesis of a pivotal prostaglandin chiral synthon via a highly enantioselective microbiological Baeyer-Villiger type reaction. Tetrahedron Lett. 30(28), 3663-3664 (1989).

    2. Ghosh, A.K., Chapsal, B.D., Baldridge, A., et al. Design and synthesis of potent HIV-1 protease inhibitors incorporating hexahydrofuropyranol-derived high affinity P2 ligands: Structure-activity studies and biological evaluation. J. Med. Chem. 54(2), 622-634 (2011).