Catalyst-free regioselective acetylation of primary hydroxy groups in partially protected and unprotected thioglycosides with acetic acid
| Parent link: | RSC Advances Vol. 10, iss. 60.— 2020.— [P. 36836-36842] |
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| Erakunde egilea: | |
| Beste egile batzuk: | , , , , , |
| Gaia: | Title screen 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-?-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. Режим доступа: по договору с организацией-держателем ресурса |
| Hizkuntza: | ingelesa |
| Argitaratua: |
2020
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| Gaiak: | |
| Sarrera elektronikoa: | https://doi.org/10.1039/D0RA07360A |
| Formatua: | Baliabide elektronikoa Liburu kapitulua |
| KOHA link: | https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=662812 |
| Gaia: | Title screen 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-?-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. Режим доступа: по договору с организацией-держателем ресурса |
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| DOI: | 10.1039/D0RA07360A |