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DOI: 10.1055/a-2648-9142
Solvent-Dependent Synthesis of Perlin Aldehyde from d-Glucal Using Ceric Ammonium Nitrate and TMSCl
Y.Y. is thankful to the Prime Minister Research Fellowship (PMRF), Ministry of Education (MoE), India. A.T. is grateful to Jawaharlal Nehru University (JNU) for merit-cum-means (MCM) scholarship. K.S. is thankful to the Council of Scientific and Industrial Research (CSIR), India for Senior Research Fellowship. The authors thank Jawaharlal Nehru University (JNU) for providing research facilities to carry out this work.
Abstract
In this study, a solvent-dependent ceric ammonium nitrate (CAN) and TMSCl-mediated synthesis of enantiopure 2,3-dideoxy-α,β-unsaturated carbohydrate enals (Perlin aldehydes) in CH3CN and 1,4-dioxane has been reported. This efficient protocol works well for the various d-glucals (O-acetyl, O-propyl, O-butyl, O-TIPS), and afforded Perlin aldehyde in acceptable to good yields. Thus, in this article we present a quick, efficient, and highly selective method for synthesizing Perlin aldehyde in 1.5 h at 70 °C in good yield.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2648-9142.
- Supporting Information
Publication History
Received: 03 May 2025
Accepted after revision: 03 July 2025
Accepted Manuscript online:
03 July 2025
Article published online:
22 July 2025
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References
- 1 Sagar R, Park J, Koh M, Park SB. J. Org. Chem. 2009; 74: 2171
- 2 Sagar R, Park SB. J. Org. Chem. 2008; 73: 3270
- 3 Yadav Y, Sagar R. Chem. Asian J. 2025; 20: e202401773
- 4 Reddy LV. R, Kumar V, Sagar R, Shaw AK. Chem. Rev. 2013; 113: 3605
- 5 Yadav Y, Tyagi R, Sagar R. Curr. Org. Chem. 2024; 29: 331
- 6 Areces P, Carrasco E, Monterde M, Light ME, Plumet J. Heterocycles 2007; 73: 857
- 7 Hirata N, Yamagiwa Y, Kamikawa T. J. Chem. Soc. 1991; 9: 2279
- 8 Galán ER, Chamizo MJ, Serrano JA. Tetrahedron Lett. 1993; 34: 1811
- 9 Rajasekaran P, Mallikharjunarao Y, Vankar YD. Synlett 2017; 28: 1346
- 10 Kinfe HH, Mebrahtu FM, Makolo FL, Moshapo PT, Manana MM. J. Org. Chem. 2014; 79: 3111
- 11 William R, Wang S, Ding F, Arviana EN, Liu XW. Angew. Chem. Int Ed. 2014; 53: 10742
- 12 Arora I, Kashyap VK, Singh AK, Dasgupta A, Kumar B, Shaw AK. Org. Biomol. Chem. 2014; 12: 6855
- 13 Gonzalez F, Lesage S, Perlin AS. Carbohydr. Res. 1975; 42: 267
- 14 Sagar R, Pathak R, Shaw AK. Carbohydr. Res. 2004; 339: 2031
- 15 Saquib M, Sagar R, Shaw AK. Carbohydr. Res. 2006; 341: 1052
- 16 Nagaraj P, Ganesan M, Ramesh NG. Tetrahedron 2011; 67: 769
- 17 Singh K, Behera SS, Tyagi R, Tiwari G, Sagar R. Carbohydr. Res. 2023; 531: 108890; DOI:
- 18 Yadav Y, Sagar R. Org. Lett. 2025; 27: 4006