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Noncatalytic selective 6-O-acetylation of methyl 2,3-di-O-benzoyl-α-d-glucopyranoside with acetic acid and acetic anhydride
Russian Chemical Bulletin ( IF 1.7 ) Pub Date : 2020-11-01 , DOI: 10.1007/s11172-020-3026-x
Y. E. Tsvetkov , M. L. Gening , N. E. Nifantiev

Noncatalytic acetylation of methyl 2,3-di- O -benzoyl-α- d -glucopyranoside with acetic acid or acetic anhydride proceeds regioselectively at the primary hydroxyl group and affords methyl 6- O -acetyl-2,3-di- O -benzoyl-α- d -glucopyranoside in good yield. The possibility of 6- O -acetylation should be taken into account when removing a 4,6- O -benzylidene protecting group with aqueous acetic acid at elevated temperature.

中文翻译:

甲基 2,3-二-O-苯甲酰基-α-d-吡喃葡萄糖苷与乙酸和乙酸酐的非催化选择性 6-O-乙酰化

甲基 2,3-二-O-苯甲酰基-α-d-吡喃葡萄糖苷与乙酸或乙酸酐的非催化乙酰化在伯羟基上区域选择性地进行,得到甲基 6-O-乙酰基-2,3-二-O-苯甲酰基-α- d -吡喃葡萄糖苷产率良好。在高温下用乙酸水溶液除去 4,6-O-亚苄基保护基团时,应考虑 6-O-乙酰化的可能性。
更新日期:2020-11-01
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