Highly alpha-selective synthesis of sialyl spirohydantoins by regiospecific domino condensation/O-->N acyl migration/N-sialylation of carbodiimides with peracetylated sialic acid.
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.
Zhang
Dengyou
D
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, People's Republic of China.
Ye
Deju
D
Feng
Enguang
E
Wang
Jinfang
J
Shi
Jianmei
J
Jiang
Hualiang
H
Liu
Hong
H
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
D002234:Carbodiimides; D006827:Hydantoins; D012794:Sialic Acids; D013141:Spiro Compounds