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. 2022 Jun 3;87(11):7474-7479.
doi: 10.1021/acs.joc.2c00206. Epub 2022 May 16.

Synthesis of a Diacetonide-Protected, Mannose-Based Oxepine: Configurational Control of Anomeric Acetate Activation

Bryant Pero  1 , Mark W Peczuh  1
Affiliations

Synthesis of a Diacetonide-Protected, Mannose-Based Oxepine: Configurational Control of Anomeric Acetate Activation

Bryant Pero et al. J Org Chem. .

Abstract

Carbohydrate-based oxepines are seven-membered-ring oxacycles containing an enol ether moiety. These compounds have been used as intermediates in the preparation of septanose carbohydrates by functionalization through their double bond. Reported here is a new synthesis of a carbohydrate based oxepine that uses 2,3;4,6-di-O-acetonide mannose as a key starting material. The oxepine is an important precursor used in the synthesis of septanose glycomimetics of mannopyranosides. The central feature of the synthesis is a two-step sequence that converts a septanose 1,2-di-O-acetate to the septanosyl bromide and onward to the oxepine via a reductive elimination.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1.
Scheme 1.. Preparation of a Methyl Septanoside from a Carbohydrate Based Oxepine
Scheme 2.
Scheme 2.. Previous Synthetic Routes to Diacetonide Mannose Oxepine 1
Scheme 3.
Scheme 3.. Preparation of Lactol 5 from D-Mannose
Scheme 4.
Scheme 4.. Revised Route to Diacetonide Mannose Oxepine 1 from Lactol 5
See this image and copyright information in PMC

References

    1. Sokol KR; Magauer T Total Synthesis of Oxepin and Dihydrooxepin Containing Natural Products. Synthesis (Stuttg). 2021, 53 (22), 4187–4202. - PMC - PubMed
    1. Barbero H; Díez-Poza C; Barbero A The Oxepane Motif in Marine Drugs. Mar. Drugs 2017, Vol. 15, Page 361 2017, 15 (11), 361. - PMC - PubMed
    1. Lu Q; Harmalkar DS; Choi Y; Lee K An Overview of Saturated Cyclic Ethers: Biological Profiles and Synthetic Strategies. Mol. 2019, Vol. 24, Page 3778 2019, 24 (20), 3778. - PMC - PubMed
    1. Sinka V; Martín VS; Cruz DA; Padrón JI Synthesis of Seven Membered Oxacycles: Recent Developments and New Approaches. Eur. J. Org. Chem. 2020, 2020 (43), 6704–6717.
    1. Kleinke AS; Webb D; Jamison TF Recent Progress in the Synthesis of Oxepanes and Medium Ring Ethers. Tetrahedron 2012, 68 (35), 6999–7018.

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