The synthesis and acid hydrolysis of methyl alpha-d-glucopyranosiduronic acid
The synthesis and acid hydrolysis of methyl alpha-d-glucopyranosiduronic acid
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甲基α-D-吡喃葡萄糖苷酸的合成及酸水解
DOI：
10.1021/jo01053a048
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发表时间：
1962
影响因子：
3.6
通讯作者：
D. B. Easty
中科院分区：
文献类型：
--
作者：
D. B. Easty
甲基-D-吡喃葡萄糖醛酸是通过甲基-D-吡喃葡萄糖苷的催化空气氧化合成的，然后：（a）将氧化产物转化为结晶甲基α-D-吡喃葡萄糖苷糖醛酸酰肼，和（b）水解酰肼以产生（甲基α-D-吡喃葡萄糖苷）糖醛酸钡。甲基-D-吡喃葡萄糖醛酸和甲基-D-吡喃葡萄糖苷在N-硫酸中在70、80和90下水解。水解结果表明糖醛酸和中性糖苷不通过相同的机制水解，并且糖醛酸没有通过显着的诱导效应而稳定。甲基-D-吡喃葡萄糖醛酸降解的研究结果支持了反应顺序：甲基-D-吡喃葡萄糖醛酸水解，然后是D-葡萄糖醛酸降解。
Methyl-D-glucopyranosiduronic acid was synthesized by a catalytic air oxidation of methyl-D-glucopyranoside followed by:(a) conversion of the oxidation product into crystalline methyl aD-glucopyranosiduronic hydrazide and (b) hydrolysis of the hydrazide toyield barium (methyl aD-glucopyranosid) uronate. Methyl-D-glucopyranosiduronic acid and methyl-D-glucopyranoside were hydrolyzed in N sulfuric acid at 70, 80, and 90. The results of the hydrolysis suggested that the uronoside and neutral glycoside did not hydrolyze via identical mechanisms and that the uronoside was not stabilized by a significant inductive effect. Results from a study of the degradation of methyl-D-glucopyranosiduronic acid support the reaction sequence: hydrolysis of methyl-D-glucopyranosiduronic acid followed by degradation of D-glucuronic acid.