Catalyst-free regioselective acetylation of primary hydroxy groups in partially protected and unprotected thioglycosides with acetic acid

Catalyst-free regioselective acetylation of primary hydroxy groups in partially protected and unprotected thioglycosides with acetic acid Full article

Journal

RSC Advances
ISSN: 2046-2069

Output data

Year: 2020, Volume: 10, Number: 60, Pages: 36836-36842 Pages count : 7 DOI: 10.1039/d0ra07360a

Authors

Abronina Polina I. ¹ , Malysheva Nelly N. ¹ , Zinin Alexander I. ¹ , Kolotyrkina Natalya G. ¹ , Stepanova Elena V. ^1,2 , Kononov Leonid O. ¹

Affiliations

1	N. K. Kochetkov Laboratory of Carbohydrate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation
2	Research School of Chemistry and Applied Biomedical Sciences, Tomsk Polytechnic University, Lenin avenue 30, Tomsk 634050, Russian Federation

Highly regioselective acetylation of primary hydroxy groups in thioglycoside derivatives with gluco- and galacto-configurations was achieved by treatment with aqueous or anhydrous acetic acid (60–100% AcOH) at elevated temperatures (80–118 °C), avoiding complex, costly and time-consuming manipulations with protective groups. Acetylation of both 4,6-O-benzylidene acetals and the corresponding diols as well as the unprotected tetraol with AcOH was shown to lead selectively to formation of 6-O-acetyl derivatives. For example, the treatment of phenyl 1-thio-β-D-glucopyranoside with anhydrous AcOH at 80 °C for 24 h gave the corresponding 6-O-acetylated derivative in 47% yield (71% based on the reacted starting material) and unreacted starting tetraol in 34% yield, which can easily be recovered by silica gel chromatography and reused in further acetylation.

Abronina P.I. , Malysheva N.N. , Zinin A.I. , Kolotyrkina N.G. , Stepanova E.V. , Kononov L.O.
Catalyst-free regioselective acetylation of primary hydroxy groups in partially protected and unprotected thioglycosides with acetic acid
RSC Advances. 2020. V.10. N60. P.36836-36842. DOI: 10.1039/d0ra07360a WOS Scopus OpenAlex

Web of science:	WOS:000576788300055
Scopus:	2-s2.0-85093101783
OpenAlex:	W3091784984

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OpenAlex	9
Scopus	7
Web of science	7