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. 2024 Nov 27;9(50):49618-49624.
doi: 10.1021/acsomega.4c07671. eCollection 2024 Dec 17.

Synthesis of N-Heteroaryl C-Glycosides and Polyhydroxylated Alkanes with Diaryl Groups from Unprotected Sugars

Yixuan Liu  1 , Jilai Wu  1   2 , Likai Zhou  1   3 , Chao Wei  1 , Hua Chen  1
Affiliations

Synthesis of N-Heteroaryl C-Glycosides and Polyhydroxylated Alkanes with Diaryl Groups from Unprotected Sugars

Yixuan Liu et al. ACS Omega. .

Abstract

HCl-catalyzed C-glycosylation was described herein for the convenient preparation of N-heteroaryl C-glycosides and polyhydroxylated alkanes with diaryl groups using hetereoaryl amines and unprotected sugars as starting materials. The reaction temperature and the amounts of aryl amines and HCl had significant effects on reactions. The method provided a highly efficient and environmentally friendly route for constructing C-glycosides at low cost.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Representative N-heteroaryl C-glycosides with good biological activities.
Scheme 1
Scheme 1. Different Methods to Synthesize Aryl C-Glycosides
Scheme 2
Scheme 2. Synthesis of 6aa
Reagents and conditions: The solution of 2,3-O-isopropylidene-d-ribose 5a (0.5 mmol, 1.0 equiv), N-methyl-3-aminopyrazole 2a (2.0 equiv), and Sc(OTf)3 (0.4 equiv) in toluene (2.5 mL)/methanol (0.5 mL) was stirred at 80 °C in a pressure tube for 3 h.
Scheme 3
Scheme 3. Control Experiments for Mechanistic Studies
Reaction conditions: aThe solution of 3ag′ (0.5 mmol, 1.0 equiv) and 1 N HCl (0.15 equiv) in toluene (1.5 mL) was stirred at 60 °C in a pressure tube for 0.5 h.
Scheme 4
Scheme 4. Plausible Reaction Mechanism for 3aa
Scheme 5
Scheme 5. Plausible Reaction Mechanism for 4aa
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