452
3
Chemical Glycosylation Reactions
compiled as well as their use in solid-phase oligosaccharide synthesis. The power of these glycosyl donors is demonstrated by their application in complex oligosaccharide and glycoconjugate synthesis, as outlined in the second part of this review. Recent applications in glycolipid,
glycosyl amino acid and glycopeptide, nucleoside and nucleotide glycosidation, glycosamino
glycan, cell wall constituent, and GPI anchor synthesis, glycosylation of various natural products and their metabolites, and finally cyclooligosaccharide generation are compiled. In the
last section, related glycosyl donors are briefly discussed.
Abbreviations
ADMB 4-acetoxy-2,2-dimethylbutanoyl
CAc
chloroacetyl
CDs
cyclodextrins
CSs
chondroitin sulfates
DBU
1,8-diazabicyclo[5.4.0]undec-7-ene
DDQ
2,3-dichloro-5,6-dicyno-benzoquinone
DMM
N-dimethylmaleoyl
DPM
diphenylmethyl
FGFs
fibroblast growth factors
Fmoc
9-fluorenylmethyl carbamate
GAGs
glycosaminoglycans
GPI
glycosylphosphatidyl inositol
HS
heparan sulfate
ILs
ionic liquids
IP
inverse procedure
IPG
inositolphosphoglycan
LTAs
lipoteichoic acids
MPEG mono-methyl polyethyleneglycol
MPLC medium pressure liquid chromatography
NAP
naphthylmethyl
PLL
photolabile linker
PNBP
p-nitrobenzylpyridine
PPTS
pyridinium p-toluenesulfonate
PTBD
polymer-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene
PS-DBU polystyrene-supported DBU
SPOS
solid-phase oligosaccharide syntheses
TBS
tert-butyl-dimethylsilyl
TMSOTf trimethylsilyl trifluoromethanesulfonate
1 Introduction
The biological significance of oligosaccharides and glycoconjugates has stimulated many
activities in carbohydrate chemistry. Most of these activities have been devoted to the development of methods for glycoside bond formation as the assembly of monosaccharide building
3
Chemical Glycosylation Reactions
compiled as well as their use in solid-phase oligosaccharide synthesis. The power of these glycosyl donors is demonstrated by their application in complex oligosaccharide and glycoconjugate synthesis, as outlined in the second part of this review. Recent applications in glycolipid,
glycosyl amino acid and glycopeptide, nucleoside and nucleotide glycosidation, glycosamino
glycan, cell wall constituent, and GPI anchor synthesis, glycosylation of various natural products and their metabolites, and finally cyclooligosaccharide generation are compiled. In the
last section, related glycosyl donors are briefly discussed.
Abbreviations
ADMB 4-acetoxy-2,2-dimethylbutanoyl
CAc
chloroacetyl
CDs
cyclodextrins
CSs
chondroitin sulfates
DBU
1,8-diazabicyclo[5.4.0]undec-7-ene
DDQ
2,3-dichloro-5,6-dicyno-benzoquinone
DMM
N-dimethylmaleoyl
DPM
diphenylmethyl
FGFs
fibroblast growth factors
Fmoc
9-fluorenylmethyl carbamate
GAGs
glycosaminoglycans
GPI
glycosylphosphatidyl inositol
HS
heparan sulfate
ILs
ionic liquids
IP
inverse procedure
IPG
inositolphosphoglycan
LTAs
lipoteichoic acids
MPEG mono-methyl polyethyleneglycol
MPLC medium pressure liquid chromatography
NAP
naphthylmethyl
PLL
photolabile linker
PNBP
p-nitrobenzylpyridine
PPTS
pyridinium p-toluenesulfonate
PTBD
polymer-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene
PS-DBU polystyrene-supported DBU
SPOS
solid-phase oligosaccharide syntheses
TBS
tert-butyl-dimethylsilyl
TMSOTf trimethylsilyl trifluoromethanesulfonate
1 Introduction
The biological significance of oligosaccharides and glycoconjugates has stimulated many
activities in carbohydrate chemistry. Most of these activities have been devoted to the development of methods for glycoside bond formation as the assembly of monosaccharide building