Synthesis of the four 1-(1-deoxy-D-pentitol-1-yl)thymines and conformational properties of the acyclic sugar chain.
Acetylated D-pentose diethyl dithioacetals were coupled by way of 1-bromo-1-ethylthio derivatives with 2,4-bis(trimethylsilyl)thymine to afford diastereomeric pairs of acyclic-sugar nucleoside analogues bearing a thymin-1-yl and an ethylthio group at C-1. Free-radical desulfurization by the action of tributylstannane removed the ethylthio group to afford the corresponding acetylated 1-(1-deoxy-d-pentitol-1-yl)thymines and subsequently the free title compounds in the arabino, lyxo, ribo, and xylo series. Conformations of the intermediates and products were studied in detail and the final products were evaluated for their potential as agents active against plant viruses and rice blast fungus.
Vejcik
Scott M
SM
Department of Chemistry, American University, 4400 Massachusetts Avenue, NW, Washington, DC 20016, USA.
Horton
Derek
D
D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D018553:Cucumis sativus / Q000187:drug effects / Q000254:growth & development / Q000821:virology; D005658:Fungi / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012275:Oryza / Q000187:drug effects / Q000382:microbiology; D010942:Plant Viruses / Q000187:drug effects; D013941:Thymine / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014026:Nicotiana / Q000187:drug effects / Q000254:growth & development / Q000821:virology
D000935:Antifungal Agents; D000998:Antiviral Agents; D002241:Carbohydrates; D013941:Thymine