20535-09-5Relevant academic research and scientific papers
Enantiopure 1,4,5-trisubstituted 1,2,3-triazoles from carbohydrates: Applications of organoselenium chemistry
Bhaumik, Atanu,Samanta, Supravat,Pathak, Tanmaya
, p. 6895 - 6904 (2014)
A wide range of stable vinyl selenone-modified furanosides has been synthesized for the first time. These 2π-partners undergo 1,3-dipolar cycloaddition reactions with a wide range of organic azides to afford enantiopure trisubstituted triazoles. Furanosyl rings opened up during triazole synthesis to generate polyfunctionalized molecules, ready to undergo further transformations. This strategy is one of the most convenient methods for the synthesis of enantiopure 1,4,5-trisubstituted 1,2,3-triazoles where the chiral components are attached to C-4 or C-5 position of triazole ring. These triazoles are formed in a regioselective manner, and several pairs of regioisomeric triazoles have also been synthesized. The approach affords densely functionalized triazoles, which are amenable to further modifications because of the presence of aldehyde and hydroxyl groups. This powerful and practical route adds to the arsenals of chemists and biologists interested in the synthesis and applications of triazoles.
Total synthesis of FK-506. Part 1: Construction of the C16-C34 fragment
Ireland, Robert E.,Liu, Longbin,Roper, Thomas D.
, p. 13221 - 13256 (2007/10/03)
The C23-C27 1,3-diol was constructed via either Brown's crotylation - osmylation or regio- and stereoselective opening of an 2,9-anhydro-β-ribofuranoside derived from D-xylofuranose. Lewis acid catalyzed epoxide opening with a protected lithiofurfural alc
The synthesis and thermodynamic equilibrium of eight 5-O-benzyl-2 (or 3)-dimethylamino-3 (or 2)-o-mesyl-α (or β)-d-xylo (or arabino) methylfuranosides
Giudicelli,Thome,Picq,Anker
, p. 5123 - 5134 (2007/10/02)
Regioselectivity of the opening of 2,3-anhydrofuranosides 1 (α and β) and 2 (α and β) by dimethylamine (and by ammonia for 1) has been determined. Thermic stability of the eight corresponding vic-dimethylaminomesylates 11-14 (α and β) in CD3CN
