title: Highly alpha-selective synthesis of sialyl spirohydantoins by regiospecific domino condensation/O-->N acyl migration/N-sialylation of carbodiimides with peracetylated sialic acid.
abstract: A novel and efficient process for the synthesis of alpha-sialyl spirohydantoin analogues via one-pot sequential reaction involving various carbodiimides and peracetylated Neu5Ac is reported. BF(3) x Et(2)O mediating intramolecular N-sialylation with excellent alpha-selectivity is first demonstrated.
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, People's Republic of China.
authors.forename: Dengyou
authors.initials: D
authors.lastname: Zhang
authors.forename: Deju
authors.initials: D
authors.lastname: Ye
authors.forename: Enguang
authors.initials: E
authors.lastname: Feng
authors.forename: Jinfang
authors.initials: J
authors.lastname: Wang
authors.forename: Jianmei
authors.initials: J
authors.lastname: Shi
authors.forename: Hualiang
authors.initials: H
authors.lastname: Jiang
authors.forename: Hong
authors.initials: H
authors.lastname: Liu
mesh_terms: D000107:Acetylation; D002234:Carbodiimides / Q000737:chemistry*; D006827:Hydantoins / Q000138:chemical synthesis*; D055601:Organic Chemistry Phenomena; D012794:Sialic Acids / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry
chemical_list: D002234:Carbodiimides; D006827:Hydantoins; D012794:Sialic Acids; D013141:Spiro Compounds