关键词: 1,4-dioxane methyl 1,2,3,4-tetra-O-acetyl-β-D-glucuronate solvent effect trimethylsilyl bis(trifluoromethanesulfonyl)imide (Tf2NTMS) β-D-glucuronidation

Mesh : Dioxanes / chemistry Solvents / chemistry Glucuronides / chemistry chemical synthesis Glycosylation Molecular Structure

来  源:   DOI:10.1248/cpb.c24-00068

Abstract:
A facile and selective β-D-glucuronidation of alcohols, such as (-)-menthol, cholestanol, (+)- and (-)-borneols, and 2-adamantanol, using commercially available methyl 1,2,3,4-tetra-O-acetyl-β-D-glucuronate as the glycosyl donor and trimethylsilyl bis(trifluoromethanesulfonyl)imide (Tf2NTMS) (0.5 equivalent) as the activator in 1,4-dioxane at 60 °C gave products in moderate yields. The addition of MS4A increased the β : α ratios of D-glucuronides when cholestanol, (+)-borneol, and 2-adamantanol were used as the acceptor substrate.
摘要:
醇的简便和选择性的β-D-葡糖醛酸化,如(-)-薄荷醇,胆固醇,(+)-和(-)-冰片,和2-金刚烷醇,使用市售的1,2,3,4-四-O-乙酰基-β-D-葡糖醛酸甲酯作为糖基供体和三甲基甲硅烷基双(三氟甲磺酰基)酰亚胺(Tf2NTMS)(0.5当量)作为活化剂在1,4-二恶烷中在60°C下得到中等产率的产物。当胆留醇时,MS4A的添加增加了D-葡糖苷酸的β:α比,(+)-冰片,和2-金刚烷醇被用作受体底物。
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