ACCEPTED MANUSCRIPT
General Procedure C, using sulfamide 4c, and purification by flash chromatography (petrol: ethyl
acetate, 2:1, R 0.4), afforded glycosylsulfamide 5c (470 mg, 77 %, α:β, 1:1) as a yellow waxy
f
-1
solid; υmax (neat) 3280 (N-H), 1350 (s, S=O), 1158 (s, S=O) cm ; δ (400 MHz, CDCl ) α anomer:
H
3
0
3
3
.89 (3H, t, J 6.7 Hz, CH ), 1.24-1.29 (14H, m, 7 x CH ), 1.48-1.53 (2H, m, NHCH CH ), 2.98-
3 2 2 2
.03 (2H, m, CH NH), 3.46-3.50 (1H, m, H-5), 3.58 (1H, dd, J5,5’ 8.6 Hz, J4,5’ 6.7 Hz, H-5’), 3.95-
2
.97 (1H, m, H-3), 3.98-4.02 (1H, m, H-2), 4.34 (1H, at, J 6.6 Hz, H-4), 4.38-4.63 (6H, m, Ph-
CH ), 5.42 (1H, d, J
10.5 Hz, H-1), 5.54 (1H, d, JNH,1 11.0 Hz NH), 7.15-7.40 (15H, m, Ar-H); β
2
NH,1
anomer: 0.89 (3H, t, J 6.7 Hz, CH ), 1.24-1.29 (14H, m, CH ), 1.48-1.53 (2H, m, NHCH CH ),
3
2
2
2
2
.98-3.03 (2H, m, CH NH), 3.52-3.54 (1H, m, H-5, H-5’), 3.95-3.97 (1H, m, H-3), 3.98-4.02 (1H,
2
m, H-2), 4.05-4.06 (1H, m, H-4), 4.38-4.63 (6H, m, Ph-CH ), 5.37 (1H, dd, JNH,1 10.2 Hz, J 4.3
2
1,2
Hz, H-1), 5.52 (1H, d, JNH,1 10.8 Hz NH), 7.15-7.40 (15H, m, Ar-H); δ (100.5 MHz, CDCl ) 14.1
C
3
(
q, CH ), 22.7, 26.7, 29.2, 29.3, 29.4, 29.5, 29.5, 31.8, (8 x t, 8 x CH ), 43.4, 43.5 (2 x t, NHCH α,
3
2
2
NHCH β), 70.1 (t, C-5α, C-5β), 71.8, 71.8, 72.0, 72.3, 73.3, 73.4 (6 x t, Ph-CH ), 80.8 (d, C-4β),
2
2
81.2, 81.8 (2 x d, C-2α, C-2β), 82.4 (d, C-3β), 83.3 (d, C-4α), 84.3 (d, C-1β), 84.8 (d, C-3α), 88.2
(d, C-1α), 127.7, 127.7, 127.7, 127.8, 127.9, 127.9, 128.1, 128.2, 128.2, 128.3, 128.4, 128.5, 128.5,
128.5, 128.6 (15 x d, 15 x Ar-C), 136.7, 136.8, 136.9, 137.4, 137.7, 137.9 (6 x s, 6 x Ar-C); HRMS
+
(
ESI) calculated for C H N NaO S: 661.3287. Found 661.3288 (MNa ).
3
6
50
2
6
3.4.24. N-(Dodecyl)-N’-(2,3,5-tri-O-benzyl-α,β-D-arabinofuranosyl)sulfamide 5d
General Procedure C, using sulfamide 4d, and purification by flash chromatography (petrol: ethyl
acetate, 2:1, R 0.4), afforded glycosylsulfamide 5d (450 mg, 71 %, α:β, 1:1) as a yellow waxy
f
-1
solid; υmax (neat) 3286 (N-H), 1344 (s, S=O), 1151 (s, S=O) cm ; δ (400 MHz, CDCl ) α anomer:
H
3
0
.89 (3H, t, J 6.9 Hz, CH ), 1.20-1.38 (18H, m, 9 x CH ), 1.44-1.65 (2H, m, CH ), 3.00 (2H, t, J 6.7
3 2 2
Hz, CH NH), 3.47 (1H, dd, J 9.8 Hz, J4,5’ 7.4 Hz, H-5), 3.58 (1H, dd, J5,5’ 9.6 Hz, J4,5’ 6.1 Hz, H-
2
5,5’
5’), 3.94-3.97 (1H, m, H-3), 3.98 (1H, at, J 3.1 Hz, H-2), 4.34 (1H, at, J 5.9 Hz, H-4), 4.40-4.67
(
6H, m, Ph-CH ), 5.42 (1H, d, JNH,1 10.5 Hz, H-1), 5.57 (1H, at, J 11.3 Hz, NH), 7.18-7.41 (15H, m,
2
Ar-H); β anomer: 0.89 (3H, t, J 6.9 Hz, CH ), 1.20-1.38 (18H, m, CH ), 1.44-1.65 (2H, m, CH ),
3
2
2
3
.00 (2H, t, J 6.7 Hz, CH NH), 3.52 (2H, d, J 5.1 Hz, H-5, H-5’), 3.94-3.97 (1H, m, H-3), 4.01 (1H,
2
at, J1,2 4.3 Hz, H-2), 4.05 (1H, dd, J4,5 5.1 Hz,J 3.5 Hz, H-4), 4.40-4.67 (6H, m, Ph-CH ), 5.37
3,4
2
(
1H, dd, JNH,1 10.2 Hz, J 4.3Hz, H-1), 5.57 (1H, t, J 11.3 Hz, NH), 7.18-7.41 (15H, m, Ar-H); δ
1
,
2
C
(
100.5 MHz, CDCl ) 14.1 (q, CH ), 22.7, 26.7, 26.7, 29.2, 29.3, 29.4, 29.6, 29.6, 29.7, 31.9 (10 x t,
3 3
1
7
0 x CH ), 43.4, 43.5 (2 x t, NHCH α, NHCH β), 70.0, 70.1(2 x t, C-5α, C-5β), 71.7, 71.8, 72.0,
2 2 2
2.3, 73.3, 73.4 (6 x t, Ph-CH ), 80.8 (d, C-4β), 81.2, 81.8 (2 x d, C-2α, C-2β), 82.4 (d, C-3β), 83.3
2
(d, C-4α), 84.3 (d, C-1β), 84.8 (d, C-3α), 88.2 (d, C-1α), 127.7, 127.7, 127.8, 127.9, 127.9, 127.9,
128.0, 128.1, 128.2, 128.2, 128.4, 128.5, 128.5, 128.5, 128.6 (15 x d, 15 x Ar-C), 136.7, 136.7,