A precursor in the synthesis of a variety of compounds
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3,4,6-Tri-O-acetyl-D-glucal

Item No. 39976

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,4,6-triacetate 1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol
CAS Number
2873-29-2
Synonyms
  • Tri-O-acetyl-D-glucal
Molecular Formula
C12H16O7
Formula Weight
272.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Sparingly soluble: 1-10 mg/mlEthanol: Sparingly soluble: 1-10 mg/ml
SMILES
CC(O[C@H]([C@H]1COC(C)=O)[C@@H](C=CO1)OC(C)=O)=O
InChi Code
InChI=1S/C12H16O7/c1-7(13)17-6-11-12(19-9(3)15)10(4-5-16-11)18-8(2)14/h4-5,10-12H,6H2,1-3H3/t10-,11-,12+/m1/s1
InChi Key
LLPWGHLVUPBSLP-UTUOFQBUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 g

    $31

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    50 g

    $59

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    100 g

    $112

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    Product Description

    3,4,6-Tri-O-acetyl-D-glucal is a derivative of D-(+)-glucose (Item No. 23733) and a precursor in the synthesis of a variety of compounds, including in the synthesis of cyclic ketene acetals and the enantioselective synthesis of spliceostatin A and thailanstatin A derivatives with spliceosome inhibitory activity.1,2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hardy, C., Levere, M.E., Kociok-Köhn, G., et al. Radical ring opening polymerization of cyclic ketene acetals derived from D-glucal. ACS Macro Lett. 12(11), 1443-1449 (2023).

    2. Ghosh, A.K., Reddy, G.C., Kovela, S., et al. Enantioselective synthesis of a cyclopropane derivative of spliceostatin A and evaluation of bioactivity. Org. Lett. 20(22), 7293-7297 (2018).

    3. Ghosh, A.K., Veitschegger, A.M., Nie, S., et al. Enantioselective synthesis of thailanstatin A methyl ester and evaluation of in vitro splicing inhibition. The Journal of Organic Chemistry 83(9), 5187-5198 (2018).