Chalcogen-containing analogs of ethylene glycol and its derivatives

Selenoacyclovir and Selenoganciclovir: Discovery of a New Template for Antiviral Agents

“…15 Treatment of 10 with selenium powder in the presence of hydrazine hydrate and KOH afforded the diselenide 11 in 90% yield. 16 The two hydroxyl groups of 11 were protected with TBDPS to yield 12. Treatment of 12 with methylene bromide in the presence of NaBH 4 produced the selenomethyl bromide 13, 17 which without purification was treated with 2-amino-6-chloropurine anion to afford the inseparable mixture of the desired N 9 -isomer 14 and its N 7isomer in 9:1 ratio (measured by 1 H NMR, 45% total yield from 12).…”

“…Synthesis began with 2-bromoethanol ( 10 ), which could be easily synthesized from ethylene glycol using the Appel reaction . Treatment of 10 with selenium powder in the presence of hydrazine hydrate and KOH afforded the diselenide 11 in 90% yield . The two hydroxyl groups of 11 were protected with TBDPS to yield 12 .…”

Synthesis of Acyclic Selenonucleoside Phosphonates as Potential Antiviral Agents

“…Ethylene glycol ( 13 ) was selectively protected with a tert ‐butyldiphenylsilyl (TBDPS) group to give 14 , which was treated with CBr 4 and Ph 3 P to afford the bromide 15 . Treatment of 15 with dipotassium diselenide, prepared in situ by reacting selenium powder with KOH in the presence of hydrazine, gave the diselenide 16 in good yield. The diselenide 16 was treated with NaBH 4 and PEG‐400 to give the selenium nucleophile 6 (X=H), which was reacted with iodide 7 to give the protected selenophosphonate 17 .…”

2‐(Pyrazol‐4‐yl)‐1,3‐oxaselenolanes from Pyrazole Сarbaldehydes and 2‐Selanyl‐1‐ethanol

“…A method for the preparation of 2‐selanyl‐1‐ethanol was proposed and successfully realized by researchers of laboratory of sulfur chemistry at the A.E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, Russia . Pyrazole carbaldehyde 1f was used as commercial product (Sigma‐Aldrich Corporate, St. Louis, MO).…”