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The Preparation and Utility of 5-β-D-Ribofuranosyl-(2H)-Tetrazole as a Key Synthon for C-Nucleoside Chemistry

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Pages 365-368 | Published online: 05 Dec 2006

References

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  • 5‐ [2,3,5‐Tri‐O‐Benzoyl‐β‐fl‐ribofuranosyl] ‐(2H)‐tetrazole (1)Sodium azide (780 mg, 12 mmoles) and ammonium chloride (12 mmoles) was added to a solution of 1‐cyano‐2,3,5‐tri‐0‐benzoyl‐β‐D‐ribofura‐nose (4.7 g, 10 mmoles) in DMF and stirred at 100° for 8h. The soiid was collected by filtration, the filtrate evaporated in vacuo and coevaporated several times with CClj, The residue was dissolved in 300 ml of EtOAc and washed with 2x30 ml of HC1/H20 (pH 1), 30 ml of a saturated solution of NaHCO, and then 30 ml of a saturated solution of NaCl. The organic layer was dried over NapSOj. to yield 4,4 g (86 %) of a solid m.p. 71–72°/ 1H NMR (CDClJ <5–4.68 (m .H H H, ); 5.74(d,1, Hi;, Jy 2/=2.3 Hz); 5.96 (m,2, H2, H3,); C, H,N; The depro‐ tection was achieved in sodium methoxide in MeQH (reflux) and the crude product crystallized from MeOH; (77 %); m.p. 282–286°) C,H,N; m/e 202,B+ = 113;NMR (D20) 5–3.79(m,2,H5, ″ ); 4.28 (dd, 1.H, .Jy 4,= 7Hz); 4.43(dd,1,H3/, J2, y= 5Hz);4.52 (dd.l.Hg„ J 2= 6Hz); 5.17 (d, 1,H./ ). Protection with 1,3‐dichloro‐ 1,1,3,3‐tetraisopropyldisiloxane v H achieved in dry pyridine (R. T., 2 ); 70 it of a foamy product m.p. 53–55°, m/e 401 (M+‐iPr)

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