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全氟苯硼酸催化的2,3-不饱和α-、β-、N-和C-连接糖苷的稳健立体选择性合成

Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated -, -, - and -linked glycosides.

作者信息

Tatina Madhu Babu, Mengxin Xia, Peilin Rao, Judeh Zaher M A

机构信息

School of Chemical and Biomedical Engineering, Nanyang Technological University, Singapore, 62 Nanyang Drive, N1.2-B1-14, Singapore 637459, Tel.: +65-6790-6738.

出版信息

Beilstein J Org Chem. 2019 Jun 11;15:1275-1280. doi: 10.3762/bjoc.15.125. eCollection 2019.

DOI:10.3762/bjoc.15.125
PMID:31293675
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6604698/
Abstract

A convenient protocol was developed for the synthesis of 2,3-unsaturated , - and -linked glycosides (enosides) using 20 mol % perflurophenylboronic acid catalyst via Ferrier rearrangement. Using this protocol, D-glucals and L-rhamnals reacted with various , - and -nucleophiles to give a wide range of glycosides in up to 98% yields with mainly α-anomeric selectivity. The perflurophenylboronic acid successfully catalyzed a wide range of substrates (both glucals and nucleophiles) under very mild reaction conditions.

摘要

开发了一种简便的方法，通过费里尔重排，使用20 mol%的全氟苯基硼酸催化剂合成2,3-不饱和的α-和β-连接糖苷（烯糖苷）。采用该方法，D-葡糖醛和L-鼠李醛与各种α-、β-和γ-亲核试剂反应，以高达98%的产率得到多种糖苷，主要具有α-异头物选择性。全氟苯基硼酸在非常温和的反应条件下成功催化了多种底物（葡糖醛和亲核试剂）。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a60/6604698/4a648f1c1674/Beilstein_J_Org_Chem-15-1275-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a60/6604698/1e05ba7bbe64/Beilstein_J_Org_Chem-15-1275-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a60/6604698/0878e0eb509a/Beilstein_J_Org_Chem-15-1275-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a60/6604698/d428147dd5a2/Beilstein_J_Org_Chem-15-1275-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a60/6604698/4a648f1c1674/Beilstein_J_Org_Chem-15-1275-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a60/6604698/1e05ba7bbe64/Beilstein_J_Org_Chem-15-1275-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a60/6604698/0878e0eb509a/Beilstein_J_Org_Chem-15-1275-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a60/6604698/d428147dd5a2/Beilstein_J_Org_Chem-15-1275-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a60/6604698/4a648f1c1674/Beilstein_J_Org_Chem-15-1275-g005.jpg

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