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Preparation of 2,3,5-Tri-O-benzyl-4-thio-L-arabino-furanosides and the Corresponding 4′-Thionucleoside Analogues (1999)

Wirsching, Jörn ; Voss, Jürgen

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 691-696

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Details

ISSN: 1434-193X

Schlagwort(e): Carbohydrates ; 4-Thiofuranosides ; Nucleosides ; Reaction mechanisms ; NOE measurements ; Chemistry ; General Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: -1-O-Acetyl-2,3,5-tri-O-benzyl-4-thio-L-arabino-furanose (9) has been prepared from D-xylose via the 1,4-dithio-L-arabino-furanoside 8. The crucial step of the reaction, i.e. the intramolecular cyclization of the open-chain dithioacetal 5, has been achieved in a yield of 90% by applying tetrabutylammonium iodide as promoter. Reaction of 9 with bis(trimethylsilyl)uracil or -thymine led to the benzyl derivatives 12 and 13 from which the deprotected 4′-thionucleoside analogues 14 and 15 have been prepared by debenzylation with boron tribromide.

Zusätzliches Material: 1 Ill.

Materialart: Digitale Medien

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