title: Highly facialselective synthesis of pyranose 1,3-oxazines and their ring opening with nucleophiles: a novel entry to 2-C-branched glycosides.
abstract: A TMSOTf-promoted cycloaddition of N-benzoyl-N,O-acetals with various glycals and 3-deoxy glycals affords pyranose 1,3-oxazines with high facial selectivity. In addition, a highly diastereoselective ring opening of the resulting pyranose 1,3-oxazines is reported. With diverse nucleophiles, these reactions take place upon heating at 80 °C. This novel ring-opening reaction affords structurally diversified 2-C-branched glycosides with three newly formed contiguous stereocenters.
authors: School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong, 510640, China. blyin@scut.edu.cn
authors: Biao-Lin
authors: BL
authors: Yin
authors: Ze-Ren
authors: ZR
authors: Zhang
authors: Li-Wen
authors: LW
authors: Xu
authors: Huanfeng
authors: H
authors: Jiang
mesh_terms: D002244:Carbon / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D015394:Molecular Structure; D010078:Oxazines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D006027:Glycosides; D010078:Oxazines; D002244:Carbon