Catalyst-free regioselective acetylation of primary hydroxy groups in partially protected and unprotected thioglycosides with acetic acid / P. I. Abronina, N. N. Malysheva, A. I. Zinin [et al.]

Уровень набора: RSC AdvancesАльтернативный автор-лицо: Abronina, P. I., Polina;Malysheva, N. N., Nelly;Zinin, A. I., Aleksandr Ivanovich;Kolotyrkina, N. G., Natalya;Stepanova, E. V., chemist, engineer of Tomsk Polytechnic University, 1978-, Elena Vladimirovna;Kononov, L. O., LeonidКоллективный автор (вторичный): Национальный исследовательский Томский политехнический университет, Исследовательская школа химических и биомедицинских технологий (ИШХБМТ), (2017- )Язык: английский.Резюме или реферат: 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..Примечания о наличии в документе библиографии/указателя: [References: 80 tit.].Аудитория: .Тематика: электронный ресурс | труды учёных ТПУ | ацетилирование | гидроксильные группы Ресурсы он-лайн:Щелкните здесь для доступа в онлайн
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[References: 80 tit.]

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.

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