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synthesis
O A selective reaction at one reactive site in a multifunctional
compound can be achieved using protective groups so that
other active sites are blocked.
O Protecting groups must fulfill a number of requirements
O React selectively in good yield
O Must be selectively removed at a later stage
O Must be non-toxic
this will react as well so it must be protected first
1. Base
2. CH 3I
Hydroxyl (OH) protecting groups
A. OH as ethers
1. Methyl ethers
O ROH ROMe
O Formation : NaH, MeI, THF or CH2N2, silica
O Cleavage : AlBr3, EtSH, Me3SiI
chemical transformations
2. Methoxymethyl ether, MOM
O R-OH R-OCH2OCH2CH2OMe
TiCl4
4. Benzyl ethers, R-Obn
O R-OH R-O-SiR3
O Formation: R3Si-Cl, pyridine, DMAP
R3Si-Cl, DCM, imidazole,
DMAP
O Cleavage: F- such as TBAF, HF
(CH3)3SiCl HF
pyridine
Ketones and aldehydes protecting groups
O Ketones and aldehydes are protected a cyclic and acyclic
ketals and acetals
O Stable to base; removed with acid
MeOH. H+
(CH2OH)2, H +
Benzene, -H2O
CH2(CH2OH)2
H+, Benzene
Amines protecting groups
O Carbamates
1. Tertiary butyl carbamate (BOC)
BOC anhydride
Pd(0), Et3SiH
3. Benzyl carbamate , CBz
(CBz-Cl)
cleavage
O Cleavage: Hydrogenolysis
O PdCl2, Et3SiH
O BBr3