Department of Chemistry, University of Florida, Gainesville, FL, 32611, United States.
Carbohydr Res. 2024 Sep;543:109223. doi: 10.1016/j.carres.2024.109223. Epub 2024 Jul 27.
The DIBAL-H reduction of the Baylis-Hillman sugar adduct, obtained from 3-O-benzyl-1,2-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose yielded trisubstituted alkenes by eliminating the β-hydroxyl group. Subsequently, the hydrolysis of the isopropylidene acetal to the corresponding hemiacetal was reacted with N-benzyl hydroxylamine hydrochloride to generate the nitrone, which underwent diastereoselective intramolecular 1,3-dipolar nitrone olefin cycloaddition (INOC) to give an isoxazolidine skeleton. The concomitant reductive cleavage of the N-O bond and benzyl group of the fused isoxazolidines afforded new functionalized aminocyclopentitols in good yields.
DIBAL-H 将 Baylis-Hillman 糖加合物还原，该加合物是由 3-O-苄基-1,2-亚异丙基-α-D-木戊吡喃糖-1,4-呋喃糖得到的，通过消除β-羟基基团生成三取代烯烃。随后，将异亚丙基缩醛水解为相应的半缩醛，与 N-苄基羟胺盐酸盐反应生成硝酮，硝酮发生非对映选择性的分子内 1,3-偶极硝酮烯烃环加成（INOC），生成异噁唑烷骨架。同时，通过还原裂解融合异噁唑烷的 N-O 键和苄基基团，以良好的收率得到新的功能化氨基环戊糖醇。
