Photolabile Protecting Group-Mediated Synthesis of 2-Deoxy-Glycosides,Chinese Journal of Chemistry

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Photolabile Protecting Group-Mediated Synthesis of 2-Deoxy-Glycosides
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2021-08-30 , DOI: 10.1002/cjoc.202100477
Xiaoqian Li ₁ , Zhi Ma ₁ , Rongkun Liu ₁ , Mattan Hurevich ₂ , You Yang ₁

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A green and efficient photolabile protecting group (PPG)-mediated glycosidation approach for the synthesis of 2-deoxy-glycosides is reported. By employing ortho-nitrobenzyl carbonate (oNBC) as PPG, N,N-dimethylformamide (DMF)-modulated SPhosAuNTf₂-promoted glycosidation with per-oNBC-protected 2-deoxy-glycosyl ynenoates affords the 2-deoxy-glycosides with moderate to excellent α-selectivities presumably depending on the reactivities of the acceptor alcohols. Based on the PPG-mediated glycosidation approach, oligosaccharides with three to six oNBC groups are effectively achieved. The multiple oNBC groups in the 2-deoxy-glycosides are completely cleaved by irradiation at 365 nm, resulting in the desired 2-deoxy-glycosides in an efficient manner without affecting the common alkyne, alkene, azide functional groups and the traditional protecting groups on the aglycones.

中文翻译：

光不稳定保护基介导的 2-脱氧糖苷合成

报道了一种用于合成 2-脱氧糖苷的绿色高效光不稳定保护基 (PPG) 介导的糖苷化方法。通过采用邻硝基苄基碳酸酯（ø NBC）作为PPG，Ñ，Ñ二甲基甲酰胺（DMF）调制SPhosAuNTf ₂促进的苷化与per- ö NBC保护的2-脱氧糖基ynenoates，得到2-脱氧-糖苷具有中等可能取决于受体醇的反应性，具有出色的 α 选择性。基于 PPG 介导的糖苷化方法，有效地实现了具有三到六个o NBC 基团的寡糖。多个o2-脱氧糖苷中的 NBC 基团通过 365 nm 的照射完全裂解，以有效的方式产生所需的 2-脱氧糖苷，而不会影响常见的炔烃、烯烃、叠氮化物官能团和苷元上的传统保护基团.

更新日期：2021-08-30

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