Two synthetic routes to 2′,3′-dideoxy-3′-C-(hydroxymethyl)-4′-thionucleosides

Autor:	Alexander C. Weymouth-Wilson, Robert J. Young, Allen J. Tench, John Mann, Sue Shaw-Ponter
Rok vydání:	1995
Předmět:	Coupling (electronics) chemistry.chemical_compound Thionucleosides chemistry Stereochemistry Hydroxymethyl
Zdroj:	J. Chem. Soc., Perkin Trans. 1. :677-681
ISSN:	1364-5463 0300-922X
Popis:	A number of 2′,3′-dideoxy-3′-C-(hydroxymethyl)-4′-thionucleosides have been prepared from either (4R, 5S)-4,5-bis(tert-butyldimethylsiloxymethyl)tetrahydrofuran-2-one or from (2R, 3R)-1-benzyloxy-3-(benzyloxymethyl)hex-5-en-2-ol. The former was converted into methyl (3R, 4S)-4-acetylsulfanyl-5-(tert-butyldimethylsiloxy)-3-(tert-butyldimethylsiloxymethyl)pentanoate and then into 1-O-acetyl-2,3-dideoxy-3-C-(tert-butyldimethylsiloxymethyl)-5-O-(tert-butyldimethylsilyl)-4-thio-D-erythro-pentofuranose prior to coupling with silylated pyrimidines. The second key intermediate was converted into (2R, 3R)-1-benzyloxy-3-benzyloxymethyl-5,5-bis(benzylsulfanyl)pentan-2-ol and thence via the mesyl ester into 1-S-benzyl-5-O-benzyl-3-C-(benzyloxymethyl)-2,3-dideoxy-1,4-dithio-D-erythro-pentofuranose prior to coupling with silylated pyrimidines.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::fef99af911c7195f005f4a3758768fb4 https://doi.org/10.1039/p19950000677 Zobrazit plný text záznamu