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. 2022 Dec;4(12):3677-3685.
doi: 10.31635/ccschem.022.202202175. Epub 2022 Dec 7.

An SN2-Type Strategy toward 1,2- cis-Furanosides

Xu Ma  1 , Yongliang Zhang  1 , Xijun Zhu  1 , Liming Zhang  1
Affiliations

An SN2-Type Strategy toward 1,2- cis-Furanosides

Xu Ma et al. CCS Chem. 2022 Dec.

Abstract

The stereoselective construction of 1,2-cis furanosidic linkage is synthetically challenging. A strategy that applies to all furanose types remains elusive. In this work, a solution is developed based on gold catalysis and the deployment of the directing-group-on-leaving-group strategy, where a basic oxazole group in the gold-activated leaving group facilitates the stereoinvertive attack by glycosyl acceptors. In addition to exhibiting good to excellent 1,2-cis selectivities, these furanosylation reactions are high-yielding and mostly complete in 30 min to 2 h. A broad range of 1,2-cis-furanosides is prepared. Although some are uncommon, the ease of access enabled by this approach presents new opportunities to study their applications in medicine and materials research.

Keywords: 1,2-cis-furanosides; SN2; furanosylation; gold catalysis; stereoselective glycosylation.

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Conflict of interest statement

Conflict of Interest The authors declare no competing financial interest.

Figures

Figure 1 |
Figure 1 |
(a) The 1,2-cis furanosidic linkages found in the cell wall hexasaccharide motifs. (b) The reactivity comparison between furanosyl and pyranosyl donors.
Figure 2 |
Figure 2 |
The stereoinvertive synthesis of xylofuranosides.
Figure 3 |
Figure 3 |
Additional donors and acceptors involved in the scope study.
Figure 4 |
Figure 4 |
The scope of SN2-type furanosylation with other pentofuranosyl donors.
Figure 5 |
Figure 5 |
The scope of SN2-type furanosylation with hexofuranosyl donors.
Scheme 1 |
Scheme 1 |
The DGLG strategy for SN2-type glycosylation leading to 1,2-cis-glycosidic bonds. DCC = N, N’-dicyclohexylcarbodiimide, DCM = dichloromethane, DMAP = 4-(dimethylamino)pyridine.
See this image and copyright information in PMC

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