Biomedical Engineering Reference
In-Depth Information
OH
OBn
O
O
HO
HO
BnO
BnO
OBn
HO
BnO
O
O
BnO
BnO
BnO
BnO
HO
O
TBDMSO
TBDMSO
HO
SEt
O
O
O
BnO
1. TASF, DMF
OH
DMTST, DTBMP
CH
2
Cl
2
2. H
2
, Pd/C
Amberlite IR-45 resin
MeOH, EtOAc
OH
O
Si
O
O
O
OH
Si
Si
Si
80%
O
O
Sucrose
quant.
S
N
N
Si
F
S
S
TfO
F
N
N
DMTST
DTBMP
TASF
SCHEME 12.50
Synthesis of sucrose employing a bridged cyclic protecting group.
12.8. CONCLUSION
Enormous progress has been made in recent years in the synthesis of complex
oligosaccharides, particularly with respect to the efficient preparation of what were
previously considered difficult linkages, and as a result the chemical synthesis of such
entities does make real contributions to biomedical science. Nevertheless, the
stereoselectivity of most glycosylation reactions does not attain the degree of
perfection required for the routine, confident adoption of automated protocols for
oligosaccharide synthesis to a large extent, as we have discussed elsewhere [136],
owing to typically unforeseen issues of mismatched donor-acceptor pairs. Accord-
ingly, the field is ripe for continued development with many challenges awaiting
imaginative solutions from creative organic chemists.
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