Synthesis of a new stable conformationally constrained 2,7-anhydrosialic acid derivative.
A stereoseletive synthesis of 2,7-anhydrosialic acid derivative 18 was achieved from d-glucono-delta-lactone. A highly syn-selective addition of Grignard reagent to theN-benzylimine 8 served as a key step.
Liu
Ke-Gang
KG
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenlin Road, Shanghai 200032, China.
Zhou
Hai-Bin
HB
Wu
Yu-Lin
YL
Yao
Zhu-Jun
ZJ
D005942:Gluconates / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D019158:N-Acetylneuraminic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D005942:Gluconates; D007783:Lactones; C106477:glucono-1,4-lactone; D019158:N-Acetylneuraminic Acid