A.I. Khodair / Carbohydrate Research 331 (2001) 445–453
1H NMR (Me2SO, CDCl3) (l)
451
Table 1 (Continued)
Compound IR (KBr) (cm−1
)
7b
7c
7e
7f
1750 (Ac), 1728 (CꢀO) 8.08–6.87 (m, 7 H, Ar), 7.04 (s, 1 H, ꢀCH), 6.06 (s, 2 H, OCH2O), 5.82 (d, J=10.20
Hz, 1 H, H-1%), 5.40 (t, J=9.15 Hz, 1 H, H-3%), 5.26 (t, J=9.90 Hz, 1 H, H-2%), 5.13
(t, J=9.90 Hz, 1 H, H-4%), 4.32–3.92 (m, 3 H, H-6%, H-5%), 2.06, 2.04, 2.02, 1.90 (3s,
12H, 4Ac)
1752 (Ac), 1727 (CꢀO) 8.08, 7.60, 7.20, 6.75 (4d, J=8.70 Hz, 8 H, Ar), 7.09 (s, 1 H, ꢀCH), 5.82 (d, J=10.50
Hz, 1 H, H-1%), 5.40 (t, J=9.30 Hz, 1 H, H-3%), 5.26 (t, J=9.75 Hz, 1 H, H-2%), 5.13
(t, J=9.75 Hz, 1 H, H-4%), 4.23–3.90 (m, 3 H, H-6%, H-5%), 3.11 (s, 6 H, NMe3), 2.07,
2.02, 1.99, 1.85 (12 H, 3s, 4Ac)
1752 (Ac), 1730 (CꢀO) 8.20–7.15 (m, 9 H, Ar), 7.11 (s, 1 H, ꢀCH), 5.83 (d, J=10.50 Hz, 1 H, H-1%), 5.42 (t,
J=9.15 Hz, 1 H, H-3%), 5.25 (t, J=9.75 Hz, 1 H, H-2%), 5.14 (t, J=9.75 Hz, 1 H,
H-4%), 4.24–3.91 (m, 3 H, H-6%, H-5%), 2.41 (s, 3 H, CH3), 2.09, 1.98, 1.94, 1.82 (4s, 12
H, 4Ac)
1750 (Ac), 1730 (CꢀO) 6.88–8.11 (m, 8 H, ꢀCH, Ar), 6.07 (s, 2 H, OCH2O), 5.82 (d, J=10.50 Hz, 1 H, H-1%),
5.40 (t, J=9.30 Hz, 1 H, H-3%), 5.25 (t, J=9.75 Hz, 1 H, H-2%), 5.18 (t, J=9.75 Hz, 1
H, 4%-H), 4.29–3.90 (m, 3 H, H-6%, H-5%), 2.41 (s, 3 H, CH3), 2.08, 2.02, 1.98, 1.88 (4s,
12 H, 4Ac)
7g
7h
1750 (Ac), 1729 (CꢀO) 8.20–6.90 (m, 9 H, ꢀCH, Ar), 5.84 (d, J=10.50 Hz, 1 H, H-1%), 5.43 (t, J=9.30 Hz, 1
H, H-3%), 5.24 (t, J=9.75 Hz, 1 H, H-2%), 5.18 (t, J=9.75 Hz, 1 H, H-4%), 4.28–3.91 (m,
3 H, H-6%, H-5%), 3.15 (s, 6 H, NMe2), 2.42 (s, 3 H, CH3), 2.08, 2.04, 2.02, 1.89 (4s, 12
H, 4Ac)
1750 (Ac), 1729 (CꢀO) 8.20–6.90 (m, 9 H, ꢀCH, Ar), 5.84 (d, J=10.50 Hz, 1 H, H-1%), 5.43 (t, J=9.30 Hz, 1
H, H-3%), 5.24 (t, J=9.75 Hz, 1 H, H-2%), 5.18 (t, J=9.75 Hz, 1 H, H-4%), 4.28–3.91 (m,
3 H, H–6%, H-5%), 3.15 (s, 6 H, NMe2), 2.42 (s, 3 H, CH3), 2.08, 2.04, 2.02, 1.89 (4s, 12
H, 4Ac)
7i
1752 (Ac), 1727 (CꢀO) 8.12–7.18 (m, 9 H, ꢀCH, Ar), 7.07 (s, 1 H, ꢀCH), 5.78 (d, J=10.50 Hz, 1 H, H-1%),
5.43 (t, J=9.15 Hz, 1 H, H-3%), 5.24 (t, J=9.75 Hz, 1 H, H-2%), 5.08 (t, J=9.75 Hz, 1
H, H-4%), 4.18–3.86 (m, 3 H, H-6%, H-5%), 2.03, 1.97, 1.95, 1.76 (4s, 12 H, 4Ac)
1751 (Ac), 1729 (CꢀO) 8.08–6.87 (m, 8 H, ꢀCH, Ar), 6.06 (s, 2 H, OCH2O), 5.80 (d, J=10.50 Hz, 1 H, H-1%),
5.40 (t, J=9.15 Hz, 1 H, H-3%), 5.22 (t, J=9.75 Hz, 1 H, H-2%), 5.15 (t, J=9.75 Hz, 1
H, H–4%), 4.32–3.93 (m, 3 H, 6%-H, 5%-H), 2.09, 2.05, 2.01, 1.89 (4s, 12 H, 4Ac)
1750 (Ac), 1731 (CꢀO) 8.09–6. 75 (m, 9 H, ꢀCH, Ar), 5.80 (d, J=10.20 Hz, 1 H, H-1%), 5.41 (t, J=9.15 Hz, 1
H, H-3%), 5.27 (t, J=9.75 Hz, 1 H, H-2%), 5.14 (t, J=9.90 Hz, 1 H, H-4%), 4.24–3.90 (m,
3 H, H-6%, H-5%), 3.12 (s, 6 H, NMe2), 2.08, 2.04, 2.02, 1.86 (4s, 12 H, 4Ac)
1751 (Ac), 1730 (CꢀO) 8.18–6.74 (m, 10 H, ꢀCH, Ar), 5.82 (d, J=10.20 Hz, 1 H, H-1%), 5.38 (t, J=9.15 Hz, 1
H, H-3%), 5.24 (t, J=9.75 Hz, 1 H, H-2%), 5.13 (t, J=9.60 Hz, 1 H, H-4%), 4.23–3.92 (m,
3 H, H-6%, H-5%), 3.01 (s, 6 H, NMe2), 2.08, 2.04, 2.00, 1.82 (4s, 12 H, 4Ac)
1750 (Ac), 1727 (CꢀO) 8.00–6.70 (m, 9 H, ꢀCH, Ar), 5.80 (d, J=10.50 Hz, 1 H, H-1%), 5.38 (t, J=9.30 Hz, 1
H, H-3%), 5.23 (t, J=9.75 Hz, 1 H, H-2%), 5.14 (t, J=9.75 Hz, 1 H, H-4%), 4.24–3.90 (m,
3 H, H-6%, H-5%), 3.20, 3.00 (2s, 12 H, 2NMe2), 2.08, 2.04, 2.02, 1.85 (4s, 12 H, 4Ac)
1752 (Ac), 1728 (CꢀO) 8.02–6.68 (m, 9 H, ꢀCH, Ar), 5.82 (d, J=10.50 Hz, 1 H, H-1%), 5.36 (t, J=9.15 Hz, 1
H, H-3%), 5.24 (t, J=9.75 Hz, 1 H, H-2%), 5.13 (t, J=9.75 Hz, 1 H, H-4%), 4.25–3.90 (m,
3 H, H-6%, H-5%), 3.09 (s, 6 H, 2NMe2), 2.08, 2.05, 2.02, 1.83 (4s, 12 H, 4Ac)
7j
7k
7l
7m
7n
9
1757, 1707 (2 CꢀO)
10.70 (s, 1 H, N-1 H), 8.00–6.24 (m, 8 H, ꢀCH, Ar), 3.83 (s, 3 H, OCH3), 2.91 (s, 6 H,
NMe2)
Method C. Compound 2a (0.36 g, 1 mmol)
heated under reflux for 1 h. Satd NaHCO3
was added to quench the reaction and the
resulting mixture was extracted with CH2Cl2.
The combined organic fractions were washed
with saturated NaCl solution, dried over
MgSO4, filtered, and evaporated to dryness.
The solid obtained was purified by flash
was suspended in anhyd MeCN (5 mL) and
BSA (0.25 mL, 1 mmol) was added, and the
reaction mixture was stirred at rt for 30 min.
1,2,3,4,6-Penta-O-acetyl-a- -glucopyranose
D
(0.39 g, 1 mmol) dissolved in anhyd MeCN
(5 mL) was added to the reaction mixture via
a canula. Finally TMSOTf (0.2 mL, 1 mmol)
was added, and the reaction mixture was
chromatography
(1:1,
diethyl
ether–
petroleum ether, bp 40–60 °C) to give 0.40 g