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OH
COOH
HO
OH
O
N
AcNH
N
N
HO
O
COOH
HO
OH
SPh
O
AcNH
HO
45
SCHEME 5.12
Sialic acid containing mimic.
alkynyl and azidoethyl groups as substituents in their anomeric chains. The reac-
tion proceeded in the presence of Cu(I) and DIPEA, and 1,2,3-triazole bridged
homo- and heterodimeric pseudo-oligosaccharides were obtained in 89-93% yields
(Scheme 5.13). The methodology was validated using sugar precursors of
gluco
-,
lacto
-, and
xylo
-configuration [35].
Field and coworkers reported the application of click chemistry to the construction
of amylopectin analogs composed of two linear maltooligosaccharide chains attached
to a maltose (Scheme 5.14) or glucose (Scheme 5.15) unit [36]. The strategy involved
OAc
O
O
O
AcO
AcO
N
OH
N
N
OAc
O
46
O
OAc
OAc
O
O
O
O
O
N
Ac
AcO
OH
N
AcO
N
OAc
O
O
AcO
47
OAc
OAc
OAc
OAc
OAc
AcO
AcO
O
O
O
O
O
O
AcO
AcO
N
OAc
N
N
OAc
48
OAc
OAc
OAc
OAc
OAc
OAc
AcO
AcO
O
O
O
O
O
O
O
O
Ac
AcO
N
OAc
AcO
N
N
OAc
AcO
49
SCHEME 5.13
Pseudoglycoconjugates.
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