Laboratoire des Glucides, FRE CNRS 3517, Université de Picardie Jules Verne, 33 rue Saint-Leu, F-80039 Amiens Cedex, France.
Carbohydr Res. 2012 Jul 15;356:115-31. doi: 10.1016/j.carres.2012.01.007. Epub 2012 Jan 24.
The synthesis of the anthrax tetrasaccharide, amenable for conjugation, has been envisaged by both [2+2] and [1+3] approaches from D-fucose and L-rhamnose. The successful route reported herein relies on a [1+3] strategy in which the 1,2-trans-glycosidic linkages have been secured using a participating group at the 2-position of the donors using conventional thio as well as trichloroacetimidate glycosylation chemistry. The exchange of the ester to benzyl protective groups on the rhamnosyl moiety was key to achieve the final assembly and functionalization of the tetrasaccharide.
炭疽四糖的合成，适合进行共轭，已经通过 D-岩藻糖和 L-鼠李糖的[2+2]和[1+3]方法来设想。本文报道的成功路线依赖于[1+3]策略，其中使用供体 2 位上的参与基团通过常规硫代和三氯乙酰亚胺糖苷化化学来确保 1,2-反式糖苷键的连接。在鼠李糖部分将酯基交换为苄基保护基是实现四糖最终组装和功能化的关键。
