N-trifluoroacetyl sialyl phosphite donors for the synthesis of alpha(2 --> 9) oligosialic acids.
[reaction: see text] A new method for the synthesis of alpha(2 --> 9) oligosialic acids is developed using phosphite sialyl donors that are protected with a C-5 N-trifluoroacetyl (NHTFA) substituent. Compared with conventional donors, these donors gave a higher degree of alpha-anomeric selectivity during glycosidic bond formation and better yields during iterative sialylation in the synthesis of oligosialic acids.
Lin
Chang-Ching
CC
Institute of Chemistry and Genomic Research Center, Academia Sinica, Taipei, Taiwan.
Huang
Kuo-Ting
KT
Lin
Chun-Cheng
CC
D002236:Carbohydrate Conformation; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D017905:Phosphites / Q000737:chemistry*; D012794:Sialic Acids / Q000138:chemical synthesis / Q000737:chemistry*
C512181:N-trifluoroacetyl sialyl phosphite; D017905:Phosphites; D012794:Sialic Acids