Synthesis of Purine and Pyrimidine 3‘-Amino-3‘-deoxy- and 3‘-Amino-2‘,3‘-dideoxyxylonucleosides

Abstract

A general procedure to obtain the 3'-aminoxylonucleosides 13a,b and 17a,b is presented. The synthetic scheme is based on the 5' directed intramolecular nucleophilic substitution at the 3'-activated position of the nucleoside. The approach of the incoming group to this position takes place regio- and stereoselectively from the most hindered face of the nucleoside. The methodology presented is applicable to ribonucleosides and 2'-deoxyribonucleosides, regardless of their nitrogenated base.

Sugar-Modified Nucleosides in Past 10 Years, A Review

“…Treatment of 9-(β-D-arabinofuranosyl)adenine 366 with Ph 3 P and DEAD in 1,4-dioxane/DMF at 70 ˚C followed by treatment of anhydro [133] dO [134] dX [143] dQ [136] dR [137] dS [138] dP [135] dT [139] dU [140] dV [141] dW [142] X = H, OH oxygen is replaced by nitrogen, was synthesized by a route based on stereospecific formation of the azasugar substrates and their subsequent coupling with a suitable nucleic base. Thus, reaction of 2,3-O-isopropylidene-D-glyceraldehyde with pyrrole derivative 372 in the presence of BF 3 ·OEt 2 gave 373, which was converted to 375 by four steps.…”

Carbonate Couplers and Functional Cyclic Carbonates from Amino Acids and Glucosamine

“…The fourth coupler 3d , bearing acetone oxime as activating group, was prepared in a one step reaction starting with glycerol carbonate chloroformate ( 5 ) and acetone oxime. Acetone oxime phenyl carbonate (acetone O ‐[phenyloxy)carbonyl]oxime) has been used for the regioselective modification of nucleotides using Lipase B from Candida antarctica (CALB); hereby the primary hydroxyl group of the saccharide unit was selectively converted to the corresponding phenyl carbonate 19. The synthetic procedure for 3d is comparable to that of 3a and b ; THF served as the solvent and dry triethylamine as acid scavenger.…”

“…Acetone oxime phenyl carbonate (acetone O-[phenyloxy)carbonyl]oxime) has been used for the regioselective modification of nucleotides using Lipase B from Candida antarctica (CALB); hereby the primary hydroxyl group of the saccharide unit was selectively converted to the corresponding phenyl carbonate. [19] The synthetic procedure for 3d is comparable to that of 3a and b; THF served as the solvent and dry triethylamine as acid scavenger. In the reaction beside the desired product 3d the tricarbonate 4 was formed and as a consequence relatively low yield (39%) of 3d was obtained.…”

Chemoenzymatic Synthesis of Novel 3‘- and 5‘-Carbazoyl Nucleoside Derivatives. Regioselective Preparation of 3‘- and 5‘-Alkylidencarbazoyl Nucleosides

“…Among the latter, ammonia, amines, amino alcohols, diamines, and amino acids were used. Hydrazine can be considered as an amine derivative and as such might react in a way similar to that described previously. 11a, Following this procedure, carbazoyl derivatives could be obtained.…”