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Keywords = silyl-Hilbert-Johnson reaction

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8 pages, 1157 KB  
Communication
Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction
by Chengyuan Liang, Weihui Ju, Shunjun Ding, Han Sun and Gennian Mao
Molecules 2017, 22(1), 84; https://doi.org/10.3390/molecules22010084 - 5 Jan 2017
Cited by 13 | Viewed by 14087
Abstract
An effective synthesis of nucleosides using glycosyl chlorides as glycosyl donors in the absence of Lewis acid has been developed. Glycosyl chlorides have been shown to be pivotal intermediates in the classical silyl-Hilbert-Johnson reaction. A possible mechanism that differs from the currently accepted [...] Read more.
An effective synthesis of nucleosides using glycosyl chlorides as glycosyl donors in the absence of Lewis acid has been developed. Glycosyl chlorides have been shown to be pivotal intermediates in the classical silyl-Hilbert-Johnson reaction. A possible mechanism that differs from the currently accepted mechanism advanced by Vorbrueggen has been proposed and verified by experiments. In practice, this catalyst-free method provides easy access to Capecitabine in high yield. Full article
(This article belongs to the Section Bioorganic Chemistry)
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13 pages, 306 KB  
Article
Synthesis of Extended Uridine Phosphonates Derived from an Allosteric P2Y2 Receptor Ligand
by Lijun Song, Martijn D. P. Risseeuw, Izet Karalic, Matthew O. Barrett, Kyle A. Brown, T. Kendall Harden and Serge Van Calenbergh
Molecules 2014, 19(4), 4313-4325; https://doi.org/10.3390/molecules19044313 - 4 Apr 2014
Cited by 5 | Viewed by 6245
Abstract
In this study we report the synthesis of C5/C6-fused uridine phosphonates that are structurally related to earlier reported allosteric P2Y2 receptor ligands. A silyl-Hilbert-Johnson reaction of six quinazoline-2,4-(1H,3H)-dione-like base moieties with a suitable ribofuranosephosphonate afforded the desired analogues [...] Read more.
In this study we report the synthesis of C5/C6-fused uridine phosphonates that are structurally related to earlier reported allosteric P2Y2 receptor ligands. A silyl-Hilbert-Johnson reaction of six quinazoline-2,4-(1H,3H)-dione-like base moieties with a suitable ribofuranosephosphonate afforded the desired analogues after full deprotection. In contrast to the parent 5-(4-fluoropheny)uridine phosphonate, the present extended-base uridine phosphonates essentially failed to modulate the P2Y2 receptor. Full article
(This article belongs to the Section Medicinal Chemistry)
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