当前位置: X-MOL 学术Beilstein. J. Org. Chem. › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose
Beilstein Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-11-25 , DOI: 10.3762/bjoc.16.237
Danny Lainé , Vincent Denavit , Olivier Lessard , Laurie Carrier , Charles-Émile Fecteau , Paul A Johnson , Denis Giguère

In this work, we have developed a simple synthetic approach using Et3N·3HF as an alternative to the DAST reagent. We controlled the stereochemistry of the nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-4-O-triflate-β-ᴅ-talopyranose using Et3N·3HF or in situ generated Et3N·1HF. The influence of the fluorine atom at C2 on reactivity at C4 could contribute to a new fluorine effect in nucleophilic substitution. Finally, with the continuous objective of synthesizing novel multi-vicinal fluorosugars, we prepared one difluorinated and one trifluorinated alditol analogue.

中文翻译:

1,6-脱水-2,3-二脱氧-2,3-二氟-β-D-六吡喃糖在C4的亲核氟化中的氟效应

在这项工作中,我们开发了一种简单的合成方法,使用Et 3 N·3HF替代DAST试剂。我们使用Et 3 N·3HF或原位生成,控制了1,6-脱水-2,3-二脱氧-2,3-二氟-4- O-三氟甲磺酸-β-ᴅ-塔拉吡喃葡萄糖在C4处的亲核氟化的立体化学Et 3 N·1HF。C2处的氟原子对C4处的反应性的影响可能有助于亲核取代中新的氟效应。最终,出于合成新型多邻位氟糖的持续目标,我们制备了一种二氟代和三氟代糖醇类似物。
更新日期:2020-11-25
down
wechat
bug