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(3×15 mL) and the combined organic phases were then dried and
the solvents evaporated. The residue was purified by column
chromatography on silica gel (CH2Cl2/MeOH, 50:1) to give 27
(35 mg, 71%). [α]2D5 = +25 (c = 1, CH Cl ). IR: ν
= 3283, 3082,
˜
max
2
2
1667, 1593, 1346, 1111, 1067, 1058, 887, 745 cm–1 1H NMR
.
(300 MHz, CDCl3): δ = 8.22–8.20 (m, 2 H, Ph), 7.12–7.10 (m, 2 H,
Ph), 5.96 (d, J1,2 = 6.9 Hz, 1 H, 1-H), 5.76 (d, JNH,2 = 6.9 Hz, 1
H, NH), 4.51 (d, J5,4 = 10.2 Hz, 1 H, 5-H), 4.48 (t, J4,3 = 10.3 Hz,
1 H, 4-H), 3.97 (t, J3,2 = 9.9 Hz,1 H, 3-H), 3.48 (dt, 1 H, 2-H),
3.35 and 3.23 (2s, 3 H each, OMe), 2.00 (s, 3 H, Me-CO), 1.35 and
1.34 (2s, 3 H each, Me) ppm. 13C NMR (125.7 MHz, CDCl3): δ =
171.1 (C=O), 161.2 (C-1 Ph), 143.7 (C-4 Ph), 126.0, 117.1 (Ph),
115.2 (CN), 100.6, 100.5 (Cq BDA), 98.3 (C-1), 68.9 (C-3), 66.0 (C-
4), 63.5 (C-5), 56.2 (C-2), 48.5, 48.3 (2 OMe), 23.6 (NHCOCH3),
17.7, 17.5 (2 CH3) ppm. FABMS: m/z = 474 (40) [M + Na]+, 420
(80) [M – OMe]+. CIMSHR: calcd. for C20H25N3O9 + H: 452.1669;
found 452.1660.
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p-Nitrophenyl 2-Acetamido-2-deoxy-β-D-glucopyranosiduronitrile
(8): Compound 27 (33 mg, 0.073 mmol) was stirred in a solution
of TFA/H2O, 2:1 (1.5 mL) for 3 h at 40 °C. The mixture was con-
centrated to give pure 8 (23 mg, 93%) as a white solid. [α]2D5 = –64
(c = 0.45, MeOH). 1H NMR (300 MHz, MeOD): δ = 8.25–8.20
(m, 2 H, Ph), 7.25–7.16 (m, 2 H, Ph), 4.58 (d, J1,2 = 8.1 Hz, 1 H,
1-H), 4.58 (d, J5,4 = 8.7 Hz, 1 H, 5-H), 3.94 (dd, J2,3 = 9.6 Hz, 1
H, 2-H), 3.68 (dd, J4,3 = 8.7 Hz, 1 H, 4-H), 3.61 (dd, 1 H, 3-H),
1.97 (s, 3 H, CH3CO) ppm. 13C NMR (75.4 MHz, MeOD): δ =
173.9 (C=O), 163.0 (C-1 Ph), 144.7 (C-4 Ph), 126.7, 117.9 (Ph),
117.5 (CN), 100.0 (C-1), 74.0, 73.4 (C-3, C-4), 67.0 (C-5), 56.9 (C-
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Supporting Information (for details see the footnote on the first
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ˇ
ˇ
(grants FRVS MSMT No. 1862/04 Nos. 203/05/0172, and 203/05/
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ˇ
MSM 6007665808, COST Chemistry D25/0001/02, MSMT OC
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