Chemistry Reference
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O
O
O
O
O
O
O
a
+
O
O
O
Si
O
O
Si
O
O
O
b
O
O
O
O
O
S
O
N
O
HO
N
O
O
N
d
O
c
O
O
O
OH
O
O
HO
OH
S
O
HO
HO
O
O
O
HO
OH
OH
HO
HO
HO
a = PABTC, AIBN, toluene, 60
o
C;b=CH
3
COOH, TBAF, THF;
c = azido-ethyl galactose, Cu(PPh
3
)
3
Br, DIPEA, DMF; d = glucothiose, HCl, DMPA, DMF
FIGURE 1.10
Synthetic strategy for the preparation of highly branched glycopolymers
devised by Perrier et al. [25].
Marra, Dondoni, et al. [27] also use both CuAAC and TEC chemistries when
synthesizing calix[4]arene-based
S
-glycoclusters. They describe the dual clustering
at the upper and lower rim of a calix[4]arene with two different sugars (galactose and
glucose) via sequential copper(I)-catalyzed azide-alkyne cycloaddition and photoin-
duced TEC. Figure 1.12 illustrates the approach.
R
R
S
S
O
H
n
H
n
O
H
n
O
O
R'N
3
O
RSH
O
O
O
O
O
O
O
O
O
R = benzyl; R' = cellobiose
R = benzyl; R' = mannose
R = hydroxyethyl; R' = galactose
N
N
N
N
Si
N
N
R = benzyl or
hydroxyethyl
R'
R'
OH
OH
HO
HO
OH
OH
cellobiose
azide
O
galactose
azide
O
H
HO
O
O
H
HO
O
HO
N
3
HO
HO
N
3
mannose azide
HO
N
3
OH
FIGURE 1.11
Haddleton and coworkers' [26] synthetic approach to end-functionalized
glycopolymers and structures of utilized carbohydrate azides.
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