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Rapid de Novo Preparation of 2,6-Dideoxy Sugar Libraries through Gold-Catalyzed Homopropargyl Orthoester Cyclization.

ABSTRACT: A flexible de novo route capable of producing libraries of 2,6-dideoxy sugars is described. We have found that Au(JackiePhos)SbF6MeCN promotes the conversion of homopropargyl orthoesters into functionalized 2,3-dihydro-4H-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.

SUBMITTER: Yalamanchili S

PROVIDER: S-EPMC6956608 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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Rapid de Novo Preparation of 2,6-Dideoxy Sugar Libraries through Gold-Catalyzed Homopropargyl Orthoester Cyclization.

Yalamanchili Subbarao S Miller William W Chen Xizhao X Bennett Clay S CS

Organic letters 20191122 23

A flexible de novo route capable of producing libraries of 2,6-dideoxy sugars is described. We have found that Au(JackiePhos)SbF6MeCN promotes the conversion of homopropargyl orthoesters into functionalized 2,3-dihydro-4H-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. ...[more]

PMID: 31755271

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