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1,6-脱水-2,3-二脱氧-2,3-二氟-β-D-己吡喃糖C4位亲核氟化反应中的氟效应

Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose.

作者信息

Lainé Danny, Denavit Vincent, Lessard Olivier, Carrier Laurie, Fecteau Charles-Émile, Johnson Paul A, Giguère Denis

机构信息

Département de chimie, Université Laval, 1045 av. De la Médecine, Québec City, Qc, G1V 0A6, Canada.

出版信息

Beilstein J Org Chem. 2020 Nov 25;16:2880-2887. doi: 10.3762/bjoc.16.237. eCollection 2020.

DOI:10.3762/bjoc.16.237
PMID:33299486
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7705882/
Abstract

In this work, we have developed a simple synthetic approach using EtN·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--triflate-β-ᴅ-talopyranose using EtN·3HF or in situ generated EtN·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.

摘要

在这项工作中，我们开发了一种简单的合成方法，使用EtN·3HF作为DAST试剂的替代品。我们使用EtN·3HF或原位生成的EtN·1HF控制了1,6-脱水-2,3-二脱氧-2,3-二氟-4-三氟甲磺酸酯-β-ᴅ-塔罗吡喃糖C4位亲核氟化的立体化学。C2位氟原子对C4位反应性的影响可能导致亲核取代中一种新的氟效应。最后，为了持续合成新型多邻位氟代糖这一目标，我们制备了一种二氟化和一种三氟化糖醇类似物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de6f/7705882/01a2215308ad/Beilstein_J_Org_Chem-16-2880-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de6f/7705882/a71f3e45d47d/Beilstein_J_Org_Chem-16-2880-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de6f/7705882/3b84e0a692ef/Beilstein_J_Org_Chem-16-2880-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de6f/7705882/b5dd4da7f0e2/Beilstein_J_Org_Chem-16-2880-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de6f/7705882/01a2215308ad/Beilstein_J_Org_Chem-16-2880-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de6f/7705882/a71f3e45d47d/Beilstein_J_Org_Chem-16-2880-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de6f/7705882/3b84e0a692ef/Beilstein_J_Org_Chem-16-2880-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de6f/7705882/b5dd4da7f0e2/Beilstein_J_Org_Chem-16-2880-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de6f/7705882/01a2215308ad/Beilstein_J_Org_Chem-16-2880-g005.jpg

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