Department of Chemical Science, Bose Institute, Block EN-80, Sector-V, Salt Lake, Kolkata, 700091, India.
Glycoconj J. 2023 Aug;40(4):449-459. doi: 10.1007/s10719-023-10122-x. Epub 2023 May 23.
A straightforward synthesis of the hexasaccharide repeating unit of the O-specific polysaccharide of Salmonella arizonae O62 was achieved in very good yield applying sequential glycosylation strategy. Successful regioselective glycosylation of the di-hydroxylated L-rhamnose moiety allowed achieving the desired compound in minimum number of synthetic steps. TEMPO catalyzed and [bis(acetoxy)iodo]benzene (BAIB) mediated late stage regioselective oxidation of a primary hydroxyl group into carboxylic acid was achieved in the hexasaccharide derivative. The glycosylation steps were high yielding with high stereochemical outcome. The desired hexasaccharide was obtained in 7% over all yield in fourteen steps starting from suitably functionalized monosaccharide intermediates.
采用顺序糖基化策略,非常有效地合成了亚利桑那沙门氏菌 O62 O-特异性多糖的六糖重复单元。通过对二羟基化 L-鼠李糖部分的成功区域选择性糖基化,以最小的合成步骤数实现了所需的化合物。在六糖衍生物中,通过 TEMPO 催化和[双(乙酰氧基)碘]苯(BAIB)介导的后期区域选择性氧化,将伯羟基氧化成羧酸。糖苷化步骤产率高,立体化学产率高。从适当官能化的单糖中间体开始,经过 14 步反应,以 7%的总收率得到了所需的六糖。