Department of Chemistry and Biochemistry, University of Missouri - St Louis, One University Boulevard, St Louis, MO 63121, USA.
Org Biomol Chem. 2020 Jul 1;18(25):4863-4871. doi: 10.1039/d0ob00803f.
The picoloyl ester (Pico) has proven to be a versatile protecting group in carbohydrate chemistry. It can be used for the purpose of stereocontrolling glycosylations via an H-bond-mediated Aglycone Delivery (HAD) method. It can also be used as a temporary protecting group that can be efficiently introduced and chemoselectively cleaved in the presence of practically all other common protecting groups used in synthesis. Herein, we will describe a new method for rapid, catalytic, and highly chemoselective removal of the picoloyl group using inexpensive copper(ii) or iron(iii) salts.
皮考酰基酯（Pico）已被证明是碳水化合物化学中一种用途广泛的保护基。它可用于通过氢键介导的糖苷基化 Aglycone Delivery（HAD）方法来控制立体化学反应。它也可用作临时保护基团，在存在实际用于合成的所有其他常见保护基团的情况下，可以有效地引入并选择性地裂解。在此，我们将描述一种使用廉价的铜（ii）或铁（iii）盐快速、催化和高度选择性去除皮考酰基的新方法。
