Fig. 2: Mechanism elucidation of the BEPT protocol in nucleoside synthesis. | Nature Communications

Fig. 2: Mechanism elucidation of the BEPT protocol in nucleoside synthesis.

From: Direct and efficient synthesis of nucleosides through the ortho-(tert-butylethynyl)phenyl thioglycosides (BEPTs) protocol

Fig. 2

A Glycosylation of 2a with MCEPT and BEPT donors (MCEPT o-(methoxycarbonylethynylphenyl)thio). B Isolation of the key catalyst intermediate II. C The chemical shift migration of H-8 of 2a’ with the increment of Au(I) catalyst amounts. D Titration of 2a’ and Au(I) catalyst (0.5 equiv) with III. E Comparison of the chemical shifts of H-8 in 2a in the presence of the same amount of III and IV (2.0 equiv). F DFT calculations (The calculations were conducted using Gaussian 09D).

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