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OH
HO
OH
O
O
HO
HO
OH
O
OH
OH
HO
68
O
O
OH
HO
O
O
propargyl bromide,
NaH, DMF, 16 h
HO
O
OH
O
O
O
O
OH
OH
O
O
O
HO
O
OH
O
OH
O
OH
HO
O
OH
69
HO
OH
OO
68
OR
RO
O
HO
OH
O
N
3
RO
OR
57
, R = H
70
OR
RO
N
N
N
, R = SO
3
Na
O
O
O
RO
CuSO
4
, NaAsc,
THF-water
OR
OH
71
72
, R = H
, R = SO
3
Na
SCHEME 6.12
Synthesis
of
-galactopyranosyl-coated
hyperbranched
hyperglycerol
(HPG) dendrimers by CuAAC.
polymer, and the subsequent nucleophilic displacement of the halogen groups by
azide anion. Poly[
p
-(azidomethyl)]styrene (
73
) [112], poly[2-azido-
-caprolactone)
(
74
) [113], and 6-azido-6-deoxy-curdlan (
75
) [114] have been prepared in this man-
ner and used in multi-CuAAC reactions with propargyl glycosides derived from
ε
-D-mannose,
-D-glucose,
-D-galactose,
N
-acetyl-
-D-glucosamine,
-maltose or
-lactose (Fig. 6.5). Coclick reactions are also possible, which has been exploited for
N
3
N
3
O
N
3
n
O
HO
O
O
O
HO
O
H
HO
O
H
O
OH
OH
N
3
OH
n
OH
n
73
74
75
N
3
FIGURE 6.5
Examples of clickable polymeric azides.
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