The effect of trifluoroacetic acid on the endocyclic cleavage of ethyl 1-thio-β-d-manno-, gluco-, galacto- and β-l-fucopyranosides with bulky silyl groups

The effect of trifluoroacetic acid on the endocyclic cleavage of ethyl 1-thio-β-d-manno-, gluco-, galacto- and β-l-fucopyranosides with bulky silyl groups Full article

Journal

Carbohydrate Research
ISSN: 1873-426X , E-ISSN: 0008-6215

Output data

Year: 2026, Volume: 568, Article number : 110045, Pages count : DOI: 10.1016/j.carres.2026.110045

Authors

Abronina Polina I. ¹ , Zinin Alexander I. ¹ , Malysheva Nelly N. ¹ , Khoroshkin Kirill V. ² , Stepanova Elena V. ³ , Kononov Leonid O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky prosp. 47, Moscow, 119991, Russian Federation
2	Tomsk State University, 36 Lenin Avenue, Tomsk, 634050, Russian Federation
3	Research School of Chemistry and Applied Biomedical Sciences, National Research Tomsk Polytechnic University, Tomsk, 634050, Russian Federation

Earlier we found that the treatment of ethyl 1-thio-β-d-galactopyranoside containing triisopropylsilyl (TIPS) groups at O-2 and O-3 with TFA–CH2Cl2 led to the corresponding 2,3-bis-O-silylated 1-thio-d-galactofuranoside. However, when ethyl 1-thio-β-d-glucopyranoside with TIPS groups at O-2 and O-3 was treated under identical acidic conditions, formation of 2,3-bis-O-silylated 1-thio-β-d-glucofuranoside was accompanied by anomerization to ethyl 1-thio-α-d-glucopyranoside. In current investigation we observed that the rearrangement of ethyl 1-thio-β-l-fucopyranoside with TIPS groups at O-2 and O-3 led to the anomeric mixture of the corresponding ethyl 1-thio-l-fucofuranosides, which can be easily separated. At the same time, the treatment of ethyl 2,3-bis-O-(triisopropylsilyl)-1-thio-β-d-mannopyranoside with TFA–CH2Cl2 resulted in anomerization to give the corresponding ethyl 1-thio-α-d-mannopyranoside. These experimental results were supported by computer modeling.

Abronina P.I. , Zinin A.I. , Malysheva N.N. , Khoroshkin K.V. , Stepanova E.V. , Kononov L.O.
The effect of trifluoroacetic acid on the endocyclic cleavage of ethyl 1-thio-β-d-manno-, gluco-, galacto- and β-l-fucopyranosides with bulky silyl groups
Carbohydrate Research. 2026. V.568. 110045 . DOI: 10.1016/j.carres.2026.110045 WOS Scopus OpenAlex

Submitted:	May 28, 2026
Published online:	Jul 25, 2026

≡ Web of science:	WOS:001835075400001
≡ Scopus:	2-s2.0-105045515985
≡ OpenAlex:	W7170079434