Functionalised tetrahydrofuran fragments from carbohydrates or sugar beet pulp biomass
Functionalised tetrahydrofuran fragments from carbohydrates or sugar beet pulp biomass
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DOI：
10.1039/c9gc00448c
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发表时间：
2019-04-21
期刊：
影响因子：
9.8
通讯作者：
Sheppard, Tom D.
中科院分区：
文献类型：
--
作者：
Benhamou, Laure;Foster, Robert W.;Sheppard, Tom D.
碳水化合物生物质代表了用于化学合成的潜在有价值的可持续原材料来源，但对于许多应用来说，有必要对存在的糖进行选择性脱氧/脱水，以获得具有有用的化学和物理性质的化合物。戊糖选择性脱水生成四氢呋喃可以通过在酸性或碱性条件下处理相应的N,N-二甲基腙来实现，两种方法显示出互补的立体选择性。脱水过程易于扩展，源自阿拉伯糖、核糖、木糖和鼠李糖的 THF 腙被转化为一系列含有伯醇、酮、羧酸或胺官能团的有用片段。这些化合物具有潜在有用的理化特性，使其适合纳入药物化学的片段/先导化合物生成库中。还表明可以从水解甜菜浆的粗样品中选择性地获得L-阿拉伯糖腙。
Carbohydrate biomass represents a potentially valuable sustainable source of raw materials for chemical synthesis, but for many applications, selective deoxygenation/dehydration of the sugars present is necessary to access compounds with useful chemical and physical properties. Selective dehydration of pentose sugars to give tetrahydrofurans can be achieved by treatment of the corresponding N,N-dimethylhydrazones under acidic or basic conditions, with the two approaches showing complementary stereoselectivity. The dehydration process is readily scalable and the THF hydrazones derived from arabinose, ribose, xylose and rhamnose were converted into a range of useful fragments containing primary alcohol, ketone, carboxylic acid or amine functional groups. These compounds have potentially useful physiochemical properties making them suitable for incorporation into fragment/lead generation libraries for medicinal chemistry. It was also shown that l-arabinose hydrazone could be obtained selectively from a crude sample of hydrolysed sugar beet pulp.