Conformationally Restricted GalN3 Donors Enable Zinc(II)-Mediated Stereocontrolled Galactosylation

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Abstract
We report a Zn(II)-mediated stereocontrolled galactosylation with two conformationally restricted GalN3 donors that enables divergent α- and β-glycosylation. The 4,6-O-TIPDS/3-O-Bz donor selectively affords α-GalN3 glycosides, while the 4,6-O-benzylidene/3-O-TIPS donor provides β-glycosides with high stereoselectivity. The methods show a broad substrate scope, good yields, and scalability and enable synthesis of GalNAc-α-Ser and the Acinetobacter baumannii CPS K45 tetrasaccharide repeating unit.
Funding Information
  • Science and Technology Planning Project of Guangdong Province (2024B1111160007)
  • Science and Technology Planning Project of Shenzen Municipality (JCYJ20241202124932044)
  • Science and Technology Planning Project of Shenzen Municipality (ZDCY20251230091801003)
  • National Natural Science Foundation of China (22577167)
  • Natural Science Foundation of Guangdong Province (2024A1515010015)
  • Shenzhen Science and Technology Innovation Program (JCYJ20241202124932044)
  • Shenzhen Science and Technology Innovation Program (ZDCY20251230091801003)
  • Shenzhen Medical Research Fund (B2602018)

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