Microwave-Enhanced Ferrier Reaction
2043
6
2
5.39 (C, Gly-C), 63.10 (C, cyclohexanol-C), 33.60 (2 C, cyclohexanol-C),
9.60 (C, cyclohexanol-C), 25.51 (2 C, cyclohexanol-C) 24.31
(
C, CH3CO), 20.91 (C, CH CO). Anal. calcd. for C H O (312): C,
3
16 24 6
6
1.52; H, 7.74. Found: C, 61.77; H, 7.98.
Ethyl 4,6-di-O-acetyl-2,3-dideoxy-threo-hex-2-eno-D-galactopyranoside
(3 m): Colorless oil. IR (neat): 2926, 1741, 1370, 1230, 1104, 1049cm ; H
21 1
NMR (CDCl ) a-configuration. d 6.11 (dd, 1 H, J ¼ 10.0, 5.6 Hz, H-3), 6.04
3
(
dd, 0.92H, J ¼ 10.0, 3.2 Hz, H-2), 5.12–5.02 (m, 2 H, H-4, H-1), 4.39–4.36
(m, 1 H, H-5), 4.25–4.22 (m, 2 H, H-6), 3.86–3.81 (m, 0.92H, OCH CH ),
2
3
3
.63–3.56 (m, 1 H, OCH CH ), 2.08, 2.07 (2 Â s, 6 H, 2 Â COCH ), 1.25
2 3
2
3
3
(
t, 3 H, OCH CH ); b-configuration. d 6.11 (dd, 1 H, J ¼ 10.0, 5.6 Hz, H-3),
5
.97 (d, 0.09H, J ¼ 10.0Hz, H-2), 5.12–5.02 (m, 2 H, H-4, H-1), 4.39–4.36
2 3
(
m, 1 H, H-5), 4.25–4.22 (m, 2 H, H-6), 3.97–3.90 (m, 0.08H, OCH CH ),
.63–3.56 (m, 1 H, OCH CH ), 2.08, 2.07 (2 Â s, 6 H, 2 Â COCH ), 1.25
2 3 3
3
2
3
3
1
t, 3 H, OCH CH ); C NMR (CDCl ): d 170.43 (C, CO), 170.19 (C, CO),
3
(
1
6
1
30.55 (C, Gly-C), 124.92 (C, Gly-C), 93.56 (C, Gly-C), 70.70 (C, Gly-C),
6.48 (C, Gly-C), 63.77 (C, Gly-C), 62.66 (C, OCH ), 20.59 (2C, CH CO),
2
3
5.05 (C, OCH CH ). Anal. calcd. for C H O (258): C, 55.81; H, 7.02.
12 18 6
2
3
Found: C, 56.02; H, 7.28.
para-t-Butylbenzyl 4,6-Di-O-acetyl-2,3-dideoxy-threo-hex-2-eno-1-thio-
a-D-galactopyranoside (3o): Colorless oil. IR (neat): 2960, 1741, 1515,
2
1 1
1
6
368, 1231, 1052, 665 cm ; H NMR (CDCl ) d 7.34–7.27 (m, 4 H, Ar-H),
3
.13–6.10 (m, 1 H, H-3), 5.99 (dd, 1 H, J ¼ 9.6, 1.2 Hz, H-2), 5.19 (d, 1 H,
J ¼ 1.2 Hz, H-1), 5.10–5.08 (m, 1 H, H-4), 4.28–4.26 (m, 2 H, H-6), 3.99–
3
.95 (m, 2 H, H-5, PhCH ), 3.77 (d, 1 H, J ¼ 13.2Hz, PhCH ), 2.16, 2.09
3 3 3
2
2
1
3
(
2 Â s, 6 H, 2 Â COCH ), 1.31–1.26 (m, 9 H, CH ); C NMR (CDCl ): d
1
1
7
3
70.40 (2 C, CO), 149.94 (C, Ar-C), 134.22 (C, Ar-C), 133.03 (2 C, Ar-C),
28.64 (C, Gly-C), 125.27 (2 C, Ar-C), 124.66 (C, Gly-C), 77.63 (C, Gly-C),
3.79 (C, Gly-C), 63.24 (C, Gly-C), 62.88 (C, Gly-C), 34.31 (C, PhCH2),
2.73 [C, C(CH ) ], 31.14 [3 C, C(CH ) ], 20.70 (2 C, CH3CO). Anal. calcd.
3
3
3 3
for C H O S (392): C, 64.26; H, 7.19. Found: C, 64.49; H, 7.38.
1 28 5
2
Ethyl 4-O-acetyl-2,3-dideoxy-threo-hex-2-eno-L-arabinopyranoside (3p):
21 1
Colorless oil. IR (neat): 2977, 1736, 1372, 1237, 1053, 959 cm ; H NMR
(
(
CDCl ) a-configuration. d 6.05–6.01 (m, 1.68 H, H-2, H-3), 5.01
3
d, 0.84 H, J ¼ 2.4 Hz, H-1), 4.96–4.94 (m, 0.84 H, H-4), 4.17 (dd, 1 H,
J ¼ 13.2, 2.8 Hz, H-5), 3.85–3.81 (m, 2 H, H-5, OCH CH ), 3.59–3.52
2
3
(m, 1 H, OCH CH ), 2.08 (s, 3 H, COCH ), 1.24 (t, 3 H, OCH CH ); b-con-
2 3 3 2 3
figuration. d 5.96–5.85 (m, 0.32 H, H-2, H-3), 5.29–5.26 (m, 0.16 H, H-4),
.95 (br s, 0.16 H, H-1), 3.87–3.81 (m, 3 H, H-5, OCH ), 3.57–3.52
4
2
1
3
(
(
(
m, 1 H, OCH ), 2.08 (s, 3 H, COCH ), 1.24 (t, 3 H, OCH CH ); C NMR
2 3 2 3
CDCl ): d 170.43 (C, CO), 170.19 (C, CO), 130.55 (C, Gly-C), 124.92
3
C, Gly-C), 93.56 (C, Gly-C), 70.70 (C, Gly-C), 66.48 (C, Gly-C), 63.77