Alternative synthetic routes to 2′,3′-didehydro-2′,3′-dideoxy-5-hydroxymethyluridine

SN- and NS-puckered sugar conformers are precursors of the (6–4) photoproduct in thymine dinucleotide

“…23 However, to our knowledge, neither 6 nor 7 , so far, have been directly prepared from the commercially available ribothymidine (5-methyluridine). Inspired by the reported divergent synthesis of 2′- O ,4′- C - and 3′- O ,4′- C -locked uridines from a uridine nucleoside, 24 we envisioned the synthesis of 6 and 7 from 2′,3′-isopropylideneribothymidine ( 8 ) 25 (Scheme 1, conditions). We only slightly modified the reported strategy 24 by using o -iodoxybenzoic acid (IBX) in acetonitrile 26 instead of the Moffatt conditions to oxidize 8 in 9 (92% yield).…”

Multi-stimuli responsive heterotypic hydrogels based on nucleolipids show selective dye adsorption

“…General procedure for the synthesis of 5 0 -O-alkylated ribothymidine (3a-3c) and uridine (4a-4c) nucleolipids Ribothymidine 2 0 ,3 0 -isopropylidene (2a) and uridine 2 0 ,3 0 -isopropylidene (2b) were synthesized by following a reported procedure. 28 Compounds 2a or 2b (1.0 equiv. ), fatty acids (dodecanoic acid, myristic acid or palmitic acid, 1.2 equiv.…”

Synthesis of 5-Hydroxymethylcytidine- and 5-Hydroxymethyl­uridine-Modified RNA

“…We conceived the synthesis of 5hm(rC) phosphoramidite 9 from nucleoside 1 [5hm(rU)] as the starting point for two reasons (Scheme 1). First, access to 5hm(rU) 1 (or derivatives thereof) has been described, [31][32][33][34][35][36] and second, we considered it desirable to introduce a divergent synthetic pathway for phosphoramidites of both nucleosides 5hm(rU) and 5hm(rC). Hence, a uracil-into-cytosine conversion was envisaged, a transformation that is well established for various pyrimidine nucleoside modifications, with a wide range of conditions accepted.…”