Strain-Release Glycosylation of Thio- and Selenoglycosides Enabled by Activation of Donor–Acceptor Oxiranes with Catalytic TfOH DOI

Xin-Yu Fang,

Liu Xingle,

Jiaying Shen

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

We have developed a strain-release glycosylation method for thio/selenoglycosides utilizing donor-acceptor oxiranes (DAOs) and triflic acid (2 mol %) via C-C bond cleavage under ambient conditions. This protocol is effective acid-sensitive sterically hindered substrates, demonstrating broad applicability. Experimental results DFT calculations reveal that DAO/TfOH-derived zwitterionic oxocarbenium species activate donors glycosyl zwitterion intermediates, facilitating glycosidic formation proton transfer. approach pioneers epoxide-mediated activation, offering mild, efficient platform diverse glycoside synthesis advancing methodologies in carbohydrate chemistry.

Language: Английский

Strain-Release Glycosylation of Thio- and Selenoglycosides Enabled by Activation of Donor–Acceptor Oxiranes with Catalytic TfOH DOI

Xin-Yu Fang,

Liu Xingle,

Jiaying Shen

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

We have developed a strain-release glycosylation method for thio/selenoglycosides utilizing donor-acceptor oxiranes (DAOs) and triflic acid (2 mol %) via C-C bond cleavage under ambient conditions. This protocol is effective acid-sensitive sterically hindered substrates, demonstrating broad applicability. Experimental results DFT calculations reveal that DAO/TfOH-derived zwitterionic oxocarbenium species activate donors glycosyl zwitterion intermediates, facilitating glycosidic formation proton transfer. approach pioneers epoxide-mediated activation, offering mild, efficient platform diverse glycoside synthesis advancing methodologies in carbohydrate chemistry.

Language: Английский

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