Synthesis of C-Glycosidic Galacturonates Suitable as Glycosyl Acceptors

• Autorzy: Vogel C. , Farouk M. , Michalik M. , Reinke H. , Jarosz S.
• Języki publikacji: EN

Abstrakty

EN

Methyl 3,4,5-tri-O-acetyl-2,6-anhydro-7,8,9-trideoxy-D-glycero-L-galacto-non-8-enonate (5) was obtained by different routes starting from D-galactose and D-galacturonic acid, respectively. Exploring several protecting group manipulations, an effective route was found out for the preparation of methyl 2,6-anhydro-5-O-benzyl-7,8,9-trideoxy- D-glycero-L-galacto-non-8-enonate (15) which is one of the key compounds in this synthetic program. Finally, selective benzylation via 3,4-O-butylstannyl intermediates resulted in methyl (16) and benzyl (17) 2,6-anhydro-4,5-di-O-benzyl-7,8,9-trideoxy-Dglycero- L-galacto-non-8-enonate both suitable as acceptors in glycosylation reactions. The chemical structure of a great number of intermediates was investigated by X-ray diffraction studies.

Słowa kluczowe

EN

D-galactose derivatives; D-galacturonic acid derivatives; oxidation

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2005
• Tom: Vol. 79 / nr 2
• Strony: 251--265
• Opis fizyczny: Bibliogr. 21 poz., rys.

Twórcy

autor

Vogel C.

• University of Rostock, Institute of Chemistry, Department of Organic Chemistry, Albert-Einstein-Straße 3a, D-18059 Rostock, Germany

autor

Farouk M.

• University of Rostock, Institute of Chemistry, Department of Organic Chemistry, Albert-Einstein-Straße 3a, D-18059 Rostock, Germany

autor

Michalik M.

• University of Rostock, Institute of Chemistry, Department of Organic Chemistry, Albert-Einstein-Straße 3a, D-18059 Rostock, Germany

autor

Reinke H.

• University of Rostock, Institute of Chemistry, Department of Organic Chemistry, Albert-Einstein-Straße 3a, D-18059 Rostock, Germany

autor

Jarosz S.

• Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, PL-01-224 Warsaw 42, Poland

Bibliografia

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