Open AccessRapid de Novo Preparation of 2,6-Dideoxy Sugar Libraries through Gold-Catalyzed Homopropargyl Orthoester Cyclization
Author(s) -
Subbarao Yalamanchili,
William T. Miller,
Xizhao Chen,
Clay S. Bennett
Publication year - 2019
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.9b03812
Subject(s) - orthoester , chemistry , sugar , catalysis , pyran , combinatorial chemistry , organic chemistry
A flexible de novo route capable of producing libraries of 2,6-dideoxy sugars is described. We have found that Au(JackiePhos)SbF 6 MeCN promotes the conversion of homopropargyl orthoesters into functionalized 2,3-dihydro-4 H -pyran-4-ones in good to excellent yields (71-90%). These latter compounds can be easily converted into a number of otherwise difficult to access 2,6-dideoxy sugars.