568
3
Chemical Glycosylation Reactions
ed 3-methoxy-2-pyridyl (MOP) glycosides have been used in glycosylation processes with
moderate success.
Keywords
2 -carboxybenzyl (CB) glycosides; 3-methoxy-2-pyridyl glycosides; Armed–disarmed;
DISAL glycosyl donors; Halonium ion transfer; Latent-active glycosylation; n-Pentenyl
glycosides; O-heteroaryl glycosyl donors; Oligosaccharide synthesis; Vinyl glycosides
Abbreviations
BCB
2-(benzyloxycarbonyl)benzyl
CAN
cerium ammonium nitrate
CB
2 -carboxybenzyl
DAST
(diethylamino)-sulfur trifluoride
DDQ
2,3-dichloro-5,6-dicyano-p-benzoquinone
DISAL
a dinitrosalicylic acid glycoside derivative
DMAP
4-(N,N-dimethylamino)pyridine
DTBMP di-tert-butylmethylpyridine
IDCP
iodonium di-sym-collidine perchlorate
MOP
3-methoxy-2-pyridyl
NBS
N-bromosuccinimide
NIS
N-iodosuccinimide
NMP
1-methylpyrrolidin-2-one
NPG
n-pentenyl glycosides
NPhth
N-phthaloyl
NPOE
n-pentenyl orthoester
PMB
p-methoxybenzyl
PMP
p-methoxyphenyl
TBAF
tetra-n-butylammonium bromide
TBAI
tetra-n-butylammonium iodide
TBSOTf tert-butyldimethylsilyl trifluoromethanesulfonate
TESOTf triethylsilyl trifluoromethanesulfonate
Tf 2 O
trifluoromethanesulfonic anhydride
TfOH
trifluoromethanesulfonic acid
THF
tetrahydrofuran
TMSOTf trimethylsilyl trifluoromethanesulfonate
TPSOTf tert-butyldiphenylsilyl trifluoromethane sulfonate
Troc
N-trichloroethoxycarbonyl
TTCP
N-tetrachlorophthaloyl
1 Introduction
From the early days, chemists involved in chemical glycosylation have been trying to develop
successful glycosyl donors. In general, the characteristics of a successful glycosyl donor might