Synthesis of 1′‐Homo‐N‐nucleosides from Hexitols

Abstract

This paper describes a new route for the synthesis of N-(1Ј-homo-L-gulitol)nucleosides and amino sugar analogues of N-(1Ј-homo-L-gulitol)nucleosides by nucleophilic epoxide ring-opening followed by O-heterocyclization of 1,2:5,6-dianhydro-3,4-di-O-benzyl-D-mannitol and 1,2:5,6-dianhydro-3,4-diazido-D-iditol, respectively. Magnesium perchlorate

Synthesis of Novel Homo-N-Nucleoside Analogs Composed of a Homo-1,4-Dioxane Sugar Analog and Substituted 1,3,5-Triazine Base Equivalents

“…The observed instability of the triazine O -nucleoside analog 2 ( Scheme 1 ), prompted us to design the potentially more stable triazine homo- N -nucleoside analogs, 4 ( Figure 5 ). N -glycosidic nucleoside analogs represent a known, well established class of stable modified nucleosides [ 33 , 34 , 35 , 36 , 37 ]. For increased stability, the linking ether group was thus replaced by the corresponding –CH 2 -NH- linker.…”

Synthesis of C‐Nucleosidic ATP Mimics as Potential FGFR3 Inhibitors

“…In the course of our study, Hanessian and coworkers14 reported the synthesis of 10 and 16 following an analogous strategy, but the epoxide opening was carried out by trimethylsilylated adenine under Lewis acid catalysis [Mg(ClO 4 ) 2 ]. However, the 1 H‐ and 13 C NMR spectroscopic data of compounds 10 and 16 were not in agreement with those reported herein 15…”

Epoxide‐Opening Cascades in the Synthesis of Polycyclic Polyether Natural Products

“…[5] This strategy was later extended into a general method for the synthesis of substituted tetrahydrofuran rings, and it is often used in preparation of biologically relevant molecules, such as nucleosides, and natural and unnatural monosaccharides. [169][170][171][172][173][174][175][176][177][178] Other early reports on epoxide-opening cascades were focused on rearrangements of topologically interesting molecules. In their pursuit of a postulated [2s+2s+2s] to [2s+2s+2s] sigmatropic rearrangement, the groups of Simmons [179,180] and Paquette [181,182] independently reported the transformation of triepoxide 64 to hexaquinane 65 under acidic conditions (Scheme 3).…”