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N
3
N
3
N
3
N
3
N
3
N
3
N
3
N
3
O
O
O
O
O
O
O
O
O
O
O
O
26
27
N
3
N
3
N
3
N
3
28
N
3
N
3
N
3
N
3
OAc
COOMe
AcO
O
Ac
CuI, DIPEA
DMF, r.t., 16 h
NaOMe, MeOH
NaOH, H
2
O
O
AcHN
S
AcO
29
HO
OH
HO
NHAc
OH
OH
COOH
HO
O
OH
OH
O
S
N
N
AcHN
S
N
N
COOH
N
OH
OH
COOH
S
N
HO
OH
N
N
N
N
NHAc
N
S
O
COOH
O
AcHN
N
HO
OH
30
HO
OH
O
O
O
O
N
N
N
N
N
N
N
N
N
N
N
N
S
HOOC
S
OH
S
O
O
S
HOOC
HO
HOOC
NHAc
HO
OH
HOOC
O
HO
HO
OH
O
NHAc
HO
OH
NHAc
NHAc
OH
HO
HO
HO
HO
31
HO
HO
32
SCHEME 6.5
Synthesis of face-selective and dual-face modified calix[4]arene click clusters
coated with neuraminic acid ligands.
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