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Synthesis of Methyl-3,4-Dideoxy-α(β)-D-glycero-hex-3-enopyranosiduloses from Levoglucosenone

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Abstract

Opening of the 1,6-anhydro bridge in levoglucosenone by the action of acetic anhydride in the presence of ZnCl2 afforded diastereoisomeric 1,6-di-O-acetyl-3,4-dideoxy-α/β-D-glycero-hex-3-enopyranos-2-uloses, and alcoholysis of the resulting diacetates in methanol, ethanol, and propan-2-ol in the presence of p-toluenesulfonic acid, camphor-10-sulfonic acid, ZnCl2, and HCl was studied. Their methanolysis in the presence of CSA gave methyl 3,4-dideoxy-α/β-D-glycero-hex-3-enopyranosid-2-uloses that are precursors to purpurosamine C and (+)-frontalin.

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Notes

  1. Hereinafter, signals of the minor diastereoisomer are given in brackets.

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ACKNOWLEDGMENTS

The authors thank Circa Group for providing commercial levoglucosenone. Spectral and analytical data were obtained using the facilities of the Chemistry joint center (Ufa Institute of Chemistry, Russian Academy of Sciences) and Agidel regional joint center (Ufa Federal Research Center, Russian Academy of Sciences).

Funding

This study was performed according to project no. AAAA-A20- 120012090028-3.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 450054, Ufa, Russia

    L. Kh. Faizullina, Yu. S. Galimova, Yu. A. Khalilova & F. A. Valeev

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  1. L. Kh. Faizullina
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  2. Yu. S. Galimova
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  3. Yu. A. Khalilova
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  4. F. A. Valeev
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Correspondence to L. Kh. Faizullina.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 7, pp. 942–948 https://doi.org/10.31857/S051474922107003X.

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Faizullina, L.K., Galimova, Y.S., Khalilova, Y.A. et al. Synthesis of Methyl-3,4-Dideoxy-α(β)-D-glycero-hex-3-enopyranosiduloses from Levoglucosenone. Russ J Org Chem 57, 1047–1052 (2021). https://doi.org/10.1134/S1070428021070034

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