title: Short synthesis of phenylpropanoid glycoside grayanoside-A and analogues.
abstract: A short synthesis of phenylethyl glycosides grayanoside-A 1, 2 and analogues 3-4 in high 43-65% overall yields is described. The main synthetic step involved regioselective O-6 acylation of unprotected 2-phenylethyl-β-D-glucoside 7 with cinnamoyl chlorides 8a-d using Me2SnCl2as catalyst. The acylation at O-6 is regioselective regardless of the type of cinnamoyl chloride used. Protection/deprotection steps of the glucoside core were not necessary. The synthetic route is generally applicable for the synthesis of phenylpropanoid glycoside class of compounds acylated at O-6.
authors.affiliation: School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, N1.2-B1-14, 637459, Singapore.
authors.forename: Duc Thinh
authors.initials: DT
authors.lastname: Khong
authors.affiliation: School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, N1.2-B1-14, 637459, Singapore. Electronic address: zaher@ntu.edu.sg.
authors.forename: Zaher M A
authors.initials: ZM
authors.lastname: Judeh
mesh_terms: D000215:Acylation; D002236:Carbohydrate Conformation; D002384:Catalysis; D005960:Glucosides / Q000138:chemical synthesis*; D006027:Glycosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical
chemical_list: D005960:Glucosides; D006027:Glycosides; C524869:grayanoside A
keywords: Grayanoside-A; Me(2)SnCl(2); Phenylpropanoid glycosides; Regioselective acylation