POSSIBLE ANTIVIRAL NUCLEOSIDES
1027
of the compound. Anal. calcd for C16H19O9N2Cl: C, 45.93; H, 4.55; N, 6.70.
Found: C, 45.81; H, 4.53; N, 6.06.
1-(2,3-Dideoxy-b-D-glycero-hexopyranosyl)thymine 6: Yield 95%; m.p.
218–220ꢀC; H NMR (CD3OD): d 8.88 (brs, 1H, -NH proton); 7.18 (brs,
1
1H, H-6); 5.88 and 5.84 (dd, 1H, H-10, J ¼ 10 Hz and 7 Hz); 5.15 (m, 1H,
H-30); 5.02 (m, 1H, H-40); 4.28 and 4.19 (dd, 2H, H-6, J ¼ 12 Hz and 6 Hz);
3.80 (m, 1H, H-50); 2.42 (m, 2H, H-20); 1.93 (s, 3H, -CH3).
Compound 7: Yield 94%; m.p. 215–219ꢀC.
Compound 8: Yield 93%; m.p. 220–222ꢀC.
1-(2,3-Dideoxy-4,6-o-benzylidene-b-D-glycero-hexopyranosyl)thymine 9:
Yield 75%; m.p. 149–152ꢀC; 1H NMR (CDCl3): d 8.65 (brs, 1H, -NH
proton); 7.23–7.16 (m, 6H, -C6H5 and H-6); 6.68 (d, 1H, H-10, J ¼ 10 Hz);
5.51 (m, 1H, H-30); 5.12 (m, 1H, H-40); 4.48 and 4.32 (two dd, 2H, H-60,
J ¼ 12 Hz and 4 Hz); 3.51 (m, 1H, H-50); 2.46 and 2.40 (two m, 2H,
Jgem ¼ 12.7 Hz, Jvic ¼ 3.05, 1.65 Hz, H-20); 1.92 (s, 3H, CH3).
Compound 10: Yield 72%; m.p. 154–155ꢀC.
Compound 11: Yield 71%; m.p. 158–161ꢀC.
1-(2,3-Dideoxy-4,6-o-benzylidene-3-o-tosyl-b-D-glycero-hexopyranosyl)-
1
thymine 12: Yield 75%; H NMR (CDCl3): d 8.70 (brs, 1H,-NH proton);
7.28–7.17 (m, 11H, 2x-C6H5 and H-6); 5.98 (d, 1H, H-10, J ¼ 12 Hz);
5.52–5.33 (m, 2H, H-30 and H-40); 4.46 and 4.31 (two dd, 2H, H-60,
J ¼ 12 Hz and 4 Hz); 3.60 (m, 1H, H-50); 2.45 and 2.41 (two m, 2H,
Jgem ¼ 12.7 Hz, Jvic ¼ 3.05, 1.65 Hz, H-20); 1.91 and 1.93 (two s, 6H, 2ꢁ- CH3).
Compound 13: Yield 75–78%; Syrup.
Compound 14: Yield 76–80%; Syrup.
1-(3-Azido-2,3-dideoxy-4,6-o-benzylidene-b-D-glycero-hexopyranosyl)thy-
mine 15: Yield 75%; m.p. 110–112ꢀC; H NMR (CDCl3): d 8.63 (brs, 1H,
1
-NH proton); 7.48–7.22 (m, 6H, -C6H5 and H-6); 6.65 (d, 1H, H-10,
J ¼ 12 Hz); 5.65–5.51 (m, 2H, H-30 and H-40); 4.58 and 4.41 (two dd, 2H,
H-60, J ¼ 10 Hz and 4 Hz); 3.54 (m, 1H, H-50); 2.46 and 2.40 (two m, 2H,
Jgem ¼ 12.8 Hz, Jvic ¼ 3.08, 1.80 Hz, H-20); 1.93 (s, 3H, CH3). IR (KBr):
2125 cmꢂ1 (N3 group).
Compound 16: Yield 72–78%; IR(Neat): 2120 cmꢂ1 (N3 group).
Compound 17: Yield 75–80%; IR(Neat): 2122 cmꢂ1 (N3 group).
1-(3-Azido-2,3-dideoxy-b-D-glycero-hexopyranosyl)thymine 18: Yield
90%; m.p. 182–185ꢀC; H NMR (CDCl3): d 8.62 (brs, 1H, -NH proton);
1
7.50 (brs, 1H, H-6); 6.68 (d, 1H, H-10, J ¼ 10 Hz); 5.64–5.46 (m, 2H, H-30
and H-40); 4.52 and 4.38 (two dd, 2H, H-60, J ¼ 12 Hz and 4 Hz); 3.62 (m,
1H, H-50); 2.48 and 2.32 (two m, 2H, H-20); 1.92 (s, 3H, CH3). IR (KBr):
2125 cmꢂ1 (N3 group).
Compound 19: Yield 85–90%; IR(Neat): 2120 cmꢂ1 (N3 group);
19F NMR (CDCl3): ꢂ 117.65.