10
M. R. AOUAD
= 7.9 Hz, H-2b), 5.11 (t, 1 H, J4,3 = J4,5 = 9.6 Hz, H-4a), 5.25 (t, 1 H, J3,2 = J3,4
= 9.6 Hz, H-3a), 5.45 (dd, 1 H, J3,2 = 9.9 Hz, J3,4 = 9.6 Hz, H-3b), 5.49 (d, 1 H,
J1,2 = 10.2 Hz, H-1a), 5.69 (dd, 1 H, J4,3 = 9.6 Hz, J4,5 = 9.9 Hz, H-4b), 6.00 (d,
1 H, J1,2 = 10.2 Hz, H-1b), 6.55 (d, 1 H, JNH,2 = 7.9 Hz, NHAc), 7.38–7.47 (m, 2 H,
Ar-H), 7.60–7.65 (m, 1 H, Ar-H), 7.72 (d, 1 H, JNH,2 = 7.9 Hz, NHAc), 7.81–7.87
(m, 1 H, Ar-H). 13C NMR (150 MHz, CDCl3), δ = 20.45, 20.65, 20.77, 20.87
C
(CH3CO), 52.78 (C-2a), 53.90 (C-2b), 62.74 (C-6a), 63.85 (C-6b), 67.19 (C-4b),
68.36 (C-4a), 70.64 (C-3b), 73.93 (C-3΄a), 74.23 (C-5b), 75.87 (C-5a), 84.70 (C-1a),
85.07 (C-1΄b), 121.96, 123.08, 123.81, 128.31, 136.22, 136.72, 150.31, 157.64 (Ar-C),
169.47, 169.87, 170.44, 170.94, 171.33, 171.48, 171.76, 172.05 (CH3CO). Anal.
Calcd. for C40H44ClN9O18S2: C, 46.27; H, 4.27; N, 12.14. Found: C, 46.39; H, 4.42;
N, 12.30. MS (ESI) m/z: 1038.15 [M+H]+.
2,2ꢀ-(5,5ꢀ-(1-(2-Chlorophenyl)-1H-1,2,3-triazole-4,5-diyl)bis
(1,3,4-oxadiazole-5,2-diyl))bis-(sulfanediyl)bis(2,3,4,6-tetra-O-acetyl-β-D-
thiogalactopyranoside) (11). This compound was obtained as colorless crystals
in 90% yield (from EtOH). Rf: 0.43 (ethylacetate/n-hexane 2:1); mp: 170–171°C.
−1
=
=
=
–
FT-IR (ꢀmax, KBr/cm ): 1566 (C C), 1631 (C N), 1739 (C O), 3051 (C H
1
Ar). H NMR (600 MHz, CDCl3), δ 1.81, 1.87, 1.92, 1.96, 1.99, 2.03, 2.10, 2.20
H
(8s, 24 H, 8 OAc), 4.03–4.11 (m, 6 H, H-5a, H-5b, H-6a, H-6b, H-6a, H-6b), 5.11
(dd, 1 H, J3,2 = 9.6 Hz, J3,4 = 4.2 Hz, H-3b), 5.15 (dd, 1 H, J3,2 = 9.2 Hz, J3,4
=
4.2 Hz, H-3a), 5.48 (dd, 1 H, J2,1 = 10.2 Hz, J2,3 = 9.2 Hz, H-2a), 5.51 (d, 1 H, J4,3
= 4.2 Hz, H-4a), 5.57 (d, 1 H, J4,3 = 4.2 Hz, H-4b), 5.62 (d, 1 H, J1,2 = 9.9 Hz,
H-1b), 5.74 (d, 1 H, J1,2 = 10.2 Hz, H-1a), 5.90 (dd, 1 H, J2,1 = 9.9 Hz, J2,3 = 9.6 Hz,
H-2b), 7.33–7.39 (m, 2 H, Ar-H), 7.72–7.80 (m, 2 H, Ar-H). 13C NMR (150 MHz,
CDCl3), δ 20.65, 20.75, 20.79, 21.02, 21.42 (CH3CO), 62.47 (C-6a), 62.93 (C-6b),
C
66.92 (C-2a), 67.32 (C-2b), 68.72 (C-4a, C-4b), 71.84 (C-3a), 72.96 (C-3b), 73.04
(C-5a), 76.24 (C-5b), 84.82 (C-1a), 86.56 (C-1b), 121.48, 122.61, 123.80, 126.31,
126.85, 127.08, 135.62, 136.07 (Ar-C), 167.02, 168.32, 169.77, 170.24, 170.46, 171.85
(CH3CO). Anal. Calcd. for C40H42ClN7O20S2: C, 46.24; H, 4.07; N, 9.42. Found: C,
46.39; H, 3.93; N, 9.56. MS (ESI) m/z: 1040.14 [M+H]+.
General procedure for the synthesis of acyclonucleoside analogs 16–19. A
solution of compound 5 (0.379 m, 1 mmol) in dry DMF (15 ml) and potassium
carbonate (0.30 g, 2.2 mmol) was stirred for two hours, and then, the appropriate
alkylating agent 12–15, 20–22 (2.2 mmol) was added. The stirring was continued
overnight. The reaction mixture was poured onto crushed ice, and the obtained
product was washed with water, dried, and recrystallized from ethanol to yield the
corresponding acyclonucleoside analog.
2,2ꢀ-(5,5ꢀ-(1-(2-Chlorophenyl)-1H-1,2,3-triazole-4,5-diyl)bis
(1,3,4-oxadiazole-5,2-diyl))bis-(sulfanediyl)diethanol (16). This compound
was obtained in−818% yield (from EtOH) as colorless crystals. mp: 172–173°C. FT-IR
=
=
–
(ꢀmax, KBr/cm ): 1572 (C C), 1609 (C N), 3026 (C H Ar), 3267–3370 (OH).
1H NMR (600 MHz, DMSO-d6), δ 3.31 (t, 2 H, J = 6.0 Hz, SCH2), 3.69–3.72 (q,
H
2 H, CH2O), 3.77–3.80 (q, 2 H, CH2O), 4.19 (t, 2 H, J = 6.0 Hz, SCH2), 5.03 (t,
1 H, J = 6.0 Hz, OH), 5.07 (t, 1 H, J = 6.0 Hz, OH), 7.43–7.87 (m, 4 H, Ar-H).