Chemistry Reference
In-Depth Information
OH
BnO
N
3
C
14
H
29
O
I
BnO
+
O
OBz
O
SH
aq NaHCO
3
TBAHS, EtOAc
rt 24h
OH
BnO
OH
BnO
O
O
O
C
25
H
51
BnO
N
3
C
14
H
29
BnO
Me
3
P/ THF. 1M NaOH
C
25
H
51
CO
2
H, EDC
CH
2
Cl
2
, rt 24h
OBz
H
N
C
14
H
29
S
OBz
O
S
O
O
O
HCl/dioxane
rt, 2h
OH
HO
OH
BnO
O
O
O
C
25
H
51
Na, NH
3
O
C
25
H
51
HO
BnO
HN
HN
H
O
O
H
OH
OBz
S
S
C
14
H
29
C
14
H
29
OH
OH
SCHEME 2.10
Zhu strategy for the synthesis of
-thioglycoside analog of KRN7000.
Scheme 2.11. The target uronic-based glycolipids were constructed with high
stereoselectivity.
Other methods [40-42] for introduction of sulfur heteroatom into multivalent
structures including glycoclusters were recently published and some of them are
reviewed by the authors of Chapters 6 and 8.
2.6 CONCLUSION AND PERSPECTIVES
The variety of new methods for thio-functionalization of small carbohydrate
molecules and more complex biomolecules via thio-click approach presented in
this review constitute a very attractive strategy for the synthesis of multiple targets
of glycoconjugates, including glycoclusters on various scaffolds, glycopeptides, and
glycoproteins.
Moreover, these powerful thio-click functionalization strategies will likely domi-
nate and compete with all other synthetic approaches available for molecular ligation
or glycoconjugation.
The recent availability of axial
-glycosyl thiols also opened the enormous oppor-
tunity for the fully stereoselective approach of thio-click functionalization for
S
-
glycosylation and protein labeling and ligation.
Furthermore, interdisciplinary attempts to utilize the high potential of thio-click
chemistry, either TEC, TYC, or TMEA in many areas of glycoscience/glycobiology
will be forthcoming. These methodologies will create a serious challenge for better
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