Chemoselective NIS/ cat. TfOH-mediated glycosylation of ethyl 2,3,4-tri-O-benzoyl-1-thio-beta-D-glucopyranoside (4) with ethyl 2,3-di-O-acetyl-5-O-benzyl-1-thio-alpha/beta-D-erythro-apiofuranoside (3) gave dimer 5 in an excellent yield. BF3Et2O-catalysed condensation of the alpha-trichloroacetimidate 18, accessible in two steps from 5, with 3,4,5-trimethoxyphenol gave beta-linked derivative 19 which could be transformed in five steps into the title compound.
Phenol, C-glycosides, bark, highly stereoselective synthesis, aryl-2-deoxy-beta-glycosides, mitsunobu reaction, cinnamomum-cassia
Publication DOI: 10.1016/S0040-4039(98)00673-XJournal NLM ID: 2984819RPublisher: Elsevier
Institutions: Leiden Institute of Chemistry, Gorlaeus Laboratories, Leiden University, Leiden, The Netherlands
Methods: 13C NMR, 1H NMR
Found