Automated fluorous-assisted solution-phase synthesis of β-1,2-, 1,3-, and 1,6-mannan oligomers.
Automated fluorous-assisted solution-phase synthesis of β-1,2-, 1,3-, and 1,6-mannan oligomers.
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DOI：
10.1016/j.carres.2016.03.025
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发表时间：
2016-07-22
影响因子：
3.1
通讯作者：
Pohl NLB
中科院分区：
文献类型：
--
作者：
Tang SL;Pohl NLB
通过应用β-定向C-5羧酸酯策略，实现了β-1，2-、1，3-和1，6-甘露聚糖低聚物的自动化液相合成。每个反应循环后的氟标记辅助纯化允许合成具有有限糖基供体负载的短β-甘露聚糖寡聚体-每个糖基化循环低至3.0当量。该研究显示了自动化溶液相合成方案用于合成各种具有挑战性的糖苷的能力，包括使用C-6酯作为保护基团，其可以在还原条件下转化为羟基用于扩链。
Automated solution-phase syntheses of β-1,2-, 1,3-, and 1,6-mannan oligomers have been accomplished by applying a β-directing C-5 carboxylate strategy. Fluorous-tag-assisted purification after each reaction cycle allowed the synthesis of short β-mannan oligomers with limited loading of glycosyl donor—as low as 3.0 equivalents for each glycosylation cycle. This study showed the capability of the automated solution-phase synthesis protocol for synthesizing various challenging glycosides, including use of a C-6 ester as a protecting group that could be converted under reductive conditions to a hydroxyl group for chain extension.