ACCEPTED MANUSCRIPT
30
D
-1
White solid (86%); m.p.:103
̊
C ;
[
α
]
= -32.4 (
̊
c 1.0, CH
2 2
Cl ); IR(cm ) 3394, 2913, 1502, 1208, 1108,
1
1
3
4
1
7
6
075, 1029, 735, 696; H NMR(CDCl
3
,500MHz, δ
): 2.25 (bs, 1H, OH), 3.56 (dd, 1H, J = 6, 9 Hz, H-6a),
.62-3.65 (m, 1H, H-4), 3.75 (s, 3H, -O-CH3), 3.90 (dd, 1H, J = 10, 2.5 Hz, H-6b), 4.07 (bs, 1H, H-3),
.14 (t, 1H, J= 6.5 Hz, 6.5 Hz, H-5), 4.31 (bs, 1H, H-2), 4.39, 4.45, 4.59, 4.75, 4.08, 4.93 (6d, 6H, J=
1.5, 12, 11.5, 11.5, 11.5, 11 Hz, 3* -O-CH Ph), 5.48 (d, 1H, J= 4 Hz, H-1), 6.79 (d, 2H, J= 9 Hz, Ar-H),
2
13
.02 (d, 2H, J= 8Hz, Ar-H) 7.23-7.42 (m, 15H, Ar-H); C NMR (CHCl
8.8 (t, C-6), 68.9 (d, C-3), 70.4 (d, C-2), 72.5 (t, Ar-C), 73.5 (t, Ar-C), 73.9 (d, C-4),74.8 (t, Ar-C), 79.6
d, C-5), 98.9 (d, C-1), 114.6, 118.7,127.7,127.8, 127.8, 127.8, 128.2, 128.3, 128.4, 128.4, 128.6 (11d,
Ar-C), 137.9, 138.2, 138.4, 155.3 (4s, Ar-C); HRMS calculated for C H O Na : 579.2353; found:
3
, 125MHz, δ): 55.6 (q, O-C),
(
33
36
7
5
79.2345.
5
.19
4-fluoro phenyl 3,4,5-tri-O-benzyl-
α-
D-galactopyranoside (5d)
30
-1
White solid (80%); m.p.:121
̊
C;
[
α
]D = -15.4
130, 1091, 1037, 742, 695; H NMR (CDCl ,500MHz,
a), 3.55 (d, 1H, J = 7.5 Hz, H-6b) , 3.72 (d, 1H, J = 12.5 Hz, H-4), 4.01-4.30 (m, 2H, H-3 & H-5), 4.36
̊
2
2
1
1
6
3
δ): 2.22 (bs, 1H, OH), 3.48 (d, 1H,J = 6.0 Hz, H-
(
bs, 1H, H-2), 4.37, 4.50, 4.51, 4.54, 4.66, 4.86 (6d, 6H, J= 10, 11.5, 11.5, 11.5, 11.5, 11.5 Hz, 3* -O-
CH Ph), 5.44 (d, 1H, J= 4 Hz, H-1), 6.88 (d, 2H, J= 7.5Hz, Ar-H), 6.96 (d, 1H, J= 8Hz, Ar-H) 7.15-7.34
2
1
3
(
m, 15H, Ar-H); C NMR (CHCl
3
, 125MHz,
3.5 (t, Ar-C), 74.9 (t, Ar-C), 76.8 (d, C-4), 79.4 (d, C-5), 98.6 (d, C-1), 115.8, 115.9, 116.0, 116.1, 116.2,
16.2, 118.6, 118.7, 127.8,127.8, 128.3 (11d, Ar-C), 137.8, 138.0, 138.3, 152.9, 157.7 (5s, Ar-C);
δ): 68.7 (t, C-6), 68.8 (d, C-3), 70.6 (d, C-2), 72.5 (t, Ar-C),
7
1
HRMS calculated for C H FO Na : 567.2153; found: 567.2147.
3
3
33
6
5
.20
4-cyano phenyl 3,4,5-tri-O-benzyl-
α-
D
-galactopyranoside (5e)
30
-1
White solid (76%); m.p.:141
̊
C;
[
α
]D = -30.5
̊
2
2
1
1
5
128, 1093, 1040, 740, 698, 474; H NMR (CDCl ,500MHz,
δ
): 2.37 (bs, 1H, OH), 3.47 (dd, 1H, J = 6,
3
.5, 9.5 Hz, H-6a), 3.58 (t, 1H, J = 7.5 Hz , 9 Hz, H-4), 3.88 (dd, 1H, J = 10, 2.5, 2 Hz, H-6b), 3.95 (t, 1H,
J= 6.5, 6.5 Hz, H-3), 4.04 (bs, 1H, H-5), 4.32 (d, 1H, J = 6 Hz, H-2), 4.34, 4.37, 4.54, 4.67, 4.76, 4.87
(
6d, 6H, J= 11.5, 11.5, 11, 11.5, 11.5, 11 Hz, 3* -O-CH Ph), 5.62 (d, 1H, J= 3.5 Hz, H-1), 7.10 (d, 2H, J=
2
1
3
8
6
.5 Hz, Ar-H), 7.14-7.36 (m, 15H, Ar-H), 7.40 (d, 1H, J= 8.5 Hz, Ar-H); C NMR (CHCl , 125MHz,
δ):
3
8.5 (t, C-6), 68.6 (d, C-3), 71.1 (d, C-2), 73.6 (t, Ar-C), 75.0 (t, Ar-C), 75.6 (t, Ar-C), 76.9 (d, C-4), 79.2
(
d, C-5), 97.5 (d, C-1), 105.9 (s, CN), 117.5 (d, Ar-C), 119.0 (s, Ar-CN), 127.9, 128.2, 128.5, 128.5,