106
2
General Synthetic Methods
PLE
pig liver esterase
PMB
p-methoxybenzyl
PMBM
p-methoxybenzyloxymethyl
PN
protease N-neutral protease
Poc
propargyloxycarbonyl
PPL
lipase from porcine pancreas
PPTS
pyridinium p-toluenesulfonate
PSE
phenylsulfonylethylidene
RJL
Rhizopus javanicus lipase
SEE
1-[2-(trimethylsilyl)ethoxy]ethyl
SEM
trimethylsilylethoxymethyl ether
SET
single electron transfer
TBS or TBDMS tert-butyldimethylsilyl
TBDPS
tert-butyldiphenylsilyl
TES
triethylsilyl
TFA
trifluoroacetic acid
TFAA
trifluoroacetic anhydride
THF
tetrahydrofurane
TIBAL
triisobutylaluminum
TIPDS
1,1,3,3-tetraisopropyldisiloxane
TIPS
trisopropylsilyl
TMEDA
tetramethylethylenediamine
TMS
trimethylsilyl
TMTr
trimethoxytriphenylmethyl
TPS
triphenylsilyl
Tr
trityl
Troc
2,2,2-trichloroethyloxycarbonyl
TBAF
tetrabutylammonium fluoride
1 Introduction
This chapter describes the chemical reactions at the oxygen atoms of carbohydrates along with
some of their fundamental characteristics. The hydroxyl groups of carbohydrates display all
the chemical properties associated with simple alcohols. The only difference is that carbohydrates contain many hydroxy groups with similar chemical character. Since the hydroxy
groups in carbohydrates play different biological roles depending on their positions, the ability to perform chemical reactions on a particular hydroxy group is highly important. However,
the regioselective transformation of one out of several hydroxy groups is far from being trivial. While the differentiation between the primary versus the secondary hydroxy groups is in
general not too difficult, the discrimination between secondary hydroxy groups is a difficult
task.
Usually, partially substituted derivatives are made with the aid of protecting groups. The protecting groups used in carbohydrate chemistry are the same as in any other area in organ-
2
General Synthetic Methods
PLE
pig liver esterase
PMB
p-methoxybenzyl
PMBM
p-methoxybenzyloxymethyl
PN
protease N-neutral protease
Poc
propargyloxycarbonyl
PPL
lipase from porcine pancreas
PPTS
pyridinium p-toluenesulfonate
PSE
phenylsulfonylethylidene
RJL
Rhizopus javanicus lipase
SEE
1-[2-(trimethylsilyl)ethoxy]ethyl
SEM
trimethylsilylethoxymethyl ether
SET
single electron transfer
TBS or TBDMS tert-butyldimethylsilyl
TBDPS
tert-butyldiphenylsilyl
TES
triethylsilyl
TFA
trifluoroacetic acid
TFAA
trifluoroacetic anhydride
THF
tetrahydrofurane
TIBAL
triisobutylaluminum
TIPDS
1,1,3,3-tetraisopropyldisiloxane
TIPS
trisopropylsilyl
TMEDA
tetramethylethylenediamine
TMS
trimethylsilyl
TMTr
trimethoxytriphenylmethyl
TPS
triphenylsilyl
Tr
trityl
Troc
2,2,2-trichloroethyloxycarbonyl
TBAF
tetrabutylammonium fluoride
1 Introduction
This chapter describes the chemical reactions at the oxygen atoms of carbohydrates along with
some of their fundamental characteristics. The hydroxyl groups of carbohydrates display all
the chemical properties associated with simple alcohols. The only difference is that carbohydrates contain many hydroxy groups with similar chemical character. Since the hydroxy
groups in carbohydrates play different biological roles depending on their positions, the ability to perform chemical reactions on a particular hydroxy group is highly important. However,
the regioselective transformation of one out of several hydroxy groups is far from being trivial. While the differentiation between the primary versus the secondary hydroxy groups is in
general not too difficult, the discrimination between secondary hydroxy groups is a difficult
task.
Usually, partially substituted derivatives are made with the aid of protecting groups. The protecting groups used in carbohydrate chemistry are the same as in any other area in organ-