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Synlett
DOI: 10.1055/a-2648-9142
letter
Emerging Trends in Organic Chemistry: A Focus on India

Solvent-Dependent Synthesis of Perlin Aldehyde from d-Glucal Using Ceric Ammonium Nitrate and TMSCl

Yogesh Yadav
,
Amul Tiwari
,
Kavita Singh
,
Ram Sagar  ∗

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.
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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.

Key words

d-glucal - ceric ammonium nitrate - TMSCl - 2-deoxy sugar - Perlin aldehyde

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2648-9142.
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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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