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extracts were evaporated. The crude product was purified using preparative TLC
(CH2Cl2/EtOH, 98/2, v/v) yielding 211 mg (50%). Rf = 0.56 (CH2Cl2/EtOH, 98/2, v/v);
[a]D = 50.1° (c = 0.33, CHCl3); IR: 2103 (N3), 1693 (C = O thym), 1651 (C = C),
1265 (C–O–C); 1H NMR (CDCl3) d: 9.12 (s, 1H, H-3), 7.27 (brs, 1H, H-6), 6.07 (t,
1H, J1’,2’ = 5.5, H-1’), 3.77 (m, 1H, H-4’), 3.63 (dd, 1H, J2’a,2’b = 13.2 Hz, H-2’a), 3.61
(dd, 1H, J3’a,3’b = 13.2 Hz, J3’a,4’ = 3.0 Hz, H-3’a), 3.51 (dd, 1H, H-2’b), 3.46 (dd, 1H,
J3’b,4’ = 5.4 Hz, H-3’b), 3.41 (dd, 1H, J5’a,5’b = 13.2 Hz, J5’a,4’ = 7.0 Hz, H-5’a), 3.35
(dd, 1H, J5’b,4’ = 4 Hz, H-5’b), 1.97 (brs, 3H, CH3); MS (DCI/NH3) m/z 358 (M Na+).
Compounds 12, 13 and 14 were prepared according to the procedure
described for 15 starting from 8 (635 mg, 1.69 mmol), 9 (146 mg, 0.40 mmol), and
10 (119 mg, 0.249 mmol), respectively.
1-[1-(1,3-Azidoisopropoxy)-2-azidoethyl]-3-tert-butoxycar-
bonylmethylthymine (12). Yield: 47.7% (364 mg); Rf = 0.74 (CH2Cl2/
EtOH, 98/2, v/v); [a]D = 94° (c = 1.23, CHCl3); IR: 2979 (C–H), 2104 (N3), 1707
1
(C = O thym), 1666 (C = O CO2tBu), 1651 (C = C), 1258 (C–O–C); H NMR
(CD3OD) d: 7.59 (d, 1H, JH6,CH3 = 1.0 Hz, H-6), 6.10 (t, 1H, J1’,2’ = 5.8 Hz, H-1’),
4.58 (s, 2H, CH2), 3.83 (m, 1H, H-4’), 3.75 (dd, 1H, J2’a,2’b = 13.1 Hz, H-2’a), 3.65
(dd, 1H, J3’a,3’b = 13.2 Hz, J3’a,4’ = 4.2 Hz, H-3’a), 3.58 (dd, 1H, H-2’b), 3.48 (dd, 1H,
J3’b,4’ = 5.5 Hz, H-3’b), 3.41 (m, 2H, H-5’a, H-5’b), 1.98 (d, 3H, JCH3,H6 = 1.0 Hz,
CH3), 1.47 (s, 9H, tBu); MS (DCI/NH3) m/z 472 (MNa+).
1-[1-(1-O-Benzoylmethyl-2-azidoethoxy)-2-azidoethyl]thymine
(13). Yield: 48% (80 mg); Rf = 0.70 (CH2Cl2/EtOH, 98/2, v/v); IR: 2940 (C–H),
2108 (N3), 1725 (C = O benzoyl), 1705 (C = O thym), 1650 (C = C), 1268 (C–O–
1
C); H NMR (CDCl3) d: 9.10 (s, 1H, H-3), 8.07–7.30 (m, 5H, Ar), 7.14 (q, 1H,
JH6,CH3 = 1.0 Hz, H-6), 6.08 (dd, 1H, J1’,2’a = 5.8 Hz, J1’,2’b = 5.1 Hz, H-1’), 4.38 (m,
1H, H-5’a), 4.37 (dd, 1H, J5’a,5’b = 12.5 Hz, J5’b,4’ = 4.8 Hz, H-5’b), 4.08 (m, 1H, H-
4’), 3.70 (dd, 1H, J3’a,3b’ = 12.8 Hz, J3’a,4’ = 5.0 Hz, H-3’a), 3.59 (dd, 1H, J3’b,4’ = 4.1
Hz, H-3’b), 3.58 (dd, 1H, J2’a,2’b = 12.8 Hz, H-2’a), 3.48 (dd, 1H, H-2’b), 1.61 (d, 3H,
JCH3,H6 = 1.0 Hz, CH3).
1-[1-(1-O-Benzoylmethyl-2-azidoethoxy)-2-azidoethyl]-3-tert-
butoxycarbonylmethyl thymine (14). Yield: 61.6% (81 mg); Rf = 0.50
(CH2Cl2/EtOH, 99/1, v/v); IR: 2925 (C–H), 2107 (N3), 1728 (C = O benzoyl), 1708
1
(C = O thym), 1670 (C = O CO2tBu), 1651 (C = C), 1271 (C–O–C); H NMR
(CD3OD) d: 7.93–7.26 (m, 5H, Ar), 7.15 (q, 1H, JH6,CH3 = 1.1 Hz, H-6), 6.11 (dd,
1H, J1’,2’a = 6.4 Hz, J1’,2’b = 4.7 Hz, H-1’), 4.54 (d, 1H, J = 16.5, CH2), 4.50 (d, IH,
J = 16.5, CH2), 4.42 (dd, 1H, J5’a,5’b = 12.2 Hz, J5’a,4’ = 6.6 Hz, H-5’a), 4.32 (dd, 1H,
J5’b,4’ = 3.28 Hz, H-5’b), 4.10 (m, 1H, H-4’), 3.70 (dd, 1H, J3a,3’b = 13.1, J3’a,4’ = 4.4
Hz, H-3’a); 3.58 (dd, 1H, J3’b,4’ = 5.8 Hz, H-3’b), 3.57 (dd, 1H, J2’a,2’b = 13.1 Hz, H-
2’a), 3.46 (dd, 1H, H-2’b), 1.61 (d, 3H, JCH3,H6 = 1.0 Hz, CH3), 1.46 (s, 9H, tBu); MS
(DCI/NH3) m/z 551 (MNa+).