Stereoselective synthesis of 1,2-cis- and 2-deoxyglycofuranosyl azides from glycosyl halides

Simple and Stereoselective Preparation of an 4‐(Aminomethyl)‐1,2,3‐triazolyl Nucleoside Phosphoramidite

“…The highest stereoselectivity observed in the formation of the azido derivative from the protected a-chloride 1 was 85%, as evidenced by 1 H-NMR. This selectivity is comparable to the published procedure that is based on a p-chlorobenzoyl-deoxyribose analog and CsN 3 or KN 3 in DMSO at room temperature (9 : 1 anomer ratio) [5]. It was found that the chromatographic separation of the a-and b-anomers is best performed for DMTr derivatives of the triazolyl nucleoside due to the noticeable difference in The configuration of the triazolyl nucleoside at C(1') was unambiguously determined by ROESY experiments for derivative 5.…”

“…-Recently, several successful examples of azideÀalkyne 1,3-dipolar cycloadditions have been reported in nucleoside and oligonucleotide chemistry [1 -4]. This relatively new method is promising for the regio-and stereoselective synthesis of substituted triazole deoxynucleosides because of the easy access to protected b-azidodeoxyribose 2 [5]. Triazolyl nucleoside derivatives have received much attention because of their potential antiviral and antitumor properties [6 -8].…”

Synthesis of glycolipopeptidic building blocks for carbohydrate receptor discovery

“…14,18,19 The glycosyl azides 1a-g were synthesized according to known procedures. [20][21][22][23][24][25][26][27] The glycosyl units 2a-h were obtained by the acylation and in situ hydrogenation 28 of 1a-h (Scheme 1).…”

A tridentate “click” nucleoside for metal-mediated base pairing

“…2-Deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentafuranosyl azide, 6-ethynyl-2,2′-bipyridine and imidazole nucleoside were synthesized according to literature procedures [31][32][33]. Phosphoramidites of the canonical nucleosides were purchased from Glen Research.…”