1448614-48-9Relevant academic research and scientific papers
Synthesis of C-septanosides from pyranoses via vinyl addition and electrophilic cyclization
Vannam, Raghu,Peczuh, Mark W.
, p. 4122 - 4125 (2013/09/12)
A two-step synthesis of C-septanosides from pyranoses is reported. Vinyl addition to tetra-O-benzyl d-glucose, d-galactose, and d-mannose gave the corresponding allylic alcohols. Electrophilic cyclization followed by treatment with iodine gave iodomethyl C-septanosides suitable for substitution reactions. The cyclizations were diastereoselective, giving cis-1,2 configured C-septanosides. Selectivity is rationalized through a model for electrophilic additions that invokes the conformation of the allylic system. This new approach should be generally applicable to the synthesis of a variety of C-septanosides.
