1122
P. J. Meloncelli et al. / Carbohydrate Research 344 (2009) 1110–1122
1.
OTMS
O
OAc
O
TMSO
TMSO
102
CH2Cl2
AcO
AcO
AcO
TMSO
O
O
I
N
N
2. nPrSH
N
N
3. Ac2O, Pyr, KHF2
20%
H
O
O
103
101
Scheme 41. Synthesis of N-(a-D-glucopyranosyl)indigo.
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sidic linkages, including O-, N- and C-glycosides. One of their main
strengths lies in the preparation of the difficult 1,2-cis O-glyco-
sides, usually offering excellent stereoselectivity, comparable or
better to those obtained with other classes of glycosyl donors.
These donors have also been used for the synthesis of other classes
of glycosidic linkages, but in many cases their advantage over other
glycosylating agents is less clear. It remains to be determined
whether this is due to undeveloped potential or limitations that
are inherent in these donors.
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