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R
R
N
N
AcO
N
3
N
N
N
N
AcO
HO
NaOH
MeOH
O
O
O
OMe
OMe
AcO
OMe
AcO
HO
AcO
AcO
HO
R
116
141-163a
141-163c
(
118
-
140
)
CuSO
4
sodium ascorbate
MW, 70ºC, 10 min
OAc
AcO
AcO
R
R
OAc
OH
AcO
HO
NaOH
MeOH
O
N
3
O
O
N
N
N
N
N
N
AcO
HO
AcO
AcO
HO
117
141-163b
141-163d
Terminal alkyne diversity sets (R)
F
3
C
n
OH
n
R
R
118
n = 1
119
n = 3
120
n = 4
121
n = 0
122
n = 1
123
n = 2
124
R = NH
2
125
R = Br
126
R = CF
3
127
R = NH
2
128
R = Br
129
R = CF
3
130
O
O
N
N
OH
N
N
O
132
133
131
134
135
OH
O
COOMe
HO
O
139
140
136
137
138
SCHEME 13.17
Synthesis of a library of 1,2,3-triazole-galactosides
141-163
, obtained
from 1,3-dipolar cycloaddition reactions as potential TcTS inhibitors.
derivatives containing galactose modified at either C-1
168
or C-6
169
positions, glu-
cose
170
or gulose
171
at C-3 positions, and by the amino acid derivative 1,2,3-triazole
fused threonine-3-
O
-galactose
172
, was obtained by Cu(I)-catalysed cycloaddition
reaction between the azido-functionalized sugars 1-N
3
-Gal
173
,6-N
3
-Gal
174
,3-N
3
-
Glc
175
and 3-N
3
-Gul
176
with the corresponding alkyne-based 2-propynyl-sialic
N
N
CF
3
N
OH
HO
N
N
HO
O
N
O
HO
OMe
HO
OH
OH
144d
153c
FIGURE 13.9
Galactose derivatives
144d
and
153c
that showed highest TcTS inhibition
and trypanocidal activity.
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