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. 2019 Dec 6;21(23):9646-9651.
doi: 10.1021/acs.orglett.9b03812. Epub 2019 Nov 22.

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

Subbarao Yalamanchili  1 , William Miller  1 , Xizhao Chen  1 , Clay S Bennett  1
Affiliations

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

Subbarao Yalamanchili et al. Org Lett. .

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.

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Figures

Figure 1.
Figure 1.
Heptadecasaccharide antibiotic saccharomicin B.
Figure 2.
Figure 2.
Possible steric interaction arising during cyclization of syn-homopropargyl orthoesters.
Scheme 1.
Scheme 1.
Proposed Synthesis and Derivatization of Enone Precursors into Hard To Access Deoxy Sugars
Scheme 2.
Scheme 2.
Synthesis of Orthoesters (−)-1, (+)-1, (+)-2, (−)-3, and (+)-3
Scheme 3.
Scheme 3.
Derivatization of Enone (−)-5 into l-Digitoxose 7 and l-Olivose 8
Scheme 4.
Scheme 4.
Derivatization of Enone (+)-6 into D-Boivinose 9 and d-Oliose 10
Scheme 5.
Scheme 5.
Derivatization of Enone (−)-5 into l-Ristosamine 11 and l-Saccharosamine 12
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