REGIOSELECTIVE ALKYLATION AND ACYLATION OF CARBOHYDRATES ENGAGED IN METAL-COMPLEXES
REGIOSELECTIVE ALKYLATION AND ACYLATION OF CARBOHYDRATES ENGAGED IN METAL-COMPLEXES
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DOI：
10.1016/0008-6215(84)85303-3
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发表时间：
1984-01-01
影响因子：
3.1
通讯作者：
SCHUERCH, C
中科院分区：
文献类型：
--
作者：
EBY, R;WEBSTER, KT;SCHUERCH, C
具有2个游离羟基的取代的碳水化合物衍生物（D-葡萄糖、D-甘露糖和D-半乳糖）通过与氢化钠和金属氯化物（铜或汞）在氧杂环戊烷或1，2-二甲氧基乙烷中反应而转化为它们的金属螯合物。这些金属螯合物与烯丙基、苄基或甲基碘，或乙酸酐或苯甲酰氯反应，得到二-、单-和未取代产物的混合物，其中1个单取代衍生物占优势。在铜螯合物的烷基化中，不存在双取代。适当选择金属离子和有机试剂通常允许在2个羟基中的任一个上选择性取代。产物通过液相色谱法分离，并通过1H-和13 C-NMR光谱进行表征。
Substituted carbohydrate derivatives (D-gluco, D-manno and D-galacto) having 2 free hydroxyl groups were converted into their metal chelates by reaction with sodium hydride and a metal chloride (cupric or mercuric) in either oxolane or 1,2-dimethoxyethane. Reaction of these metal chelates with allyl, benzyl or methyl iodide, or acetic anhydride or benzoyl chloride, gave a mixture of di-, mono- and un-substituted products in which 1 monosubstituted derivative preponderated. In the alkylation of copper chelates, disubstitution was absent. Appropriate choice of metal ion and organic reagent often permits selective substitution on either of 2 hydroxyl groups. Products were separated by liquid chromatography, and characterized by 1H- and 13C-NMR spectroscopy.