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Mild and Selective Reagents for Cleavage of Protecting Groups
No.107(January 2003)

The reagents 1, which are Lewis acids, selectively cleave certain ether, ester and carbamate protecting groups under mild conditions.1) The relative reactivity of common protecting groups towards 1 was reported:1a) MOMOR, MEMOR > BOC > CBZ, tBuOR > PhCH2OR > CH2=CHCH2OR > tBuO2CR, secondary alkylOR > PhCH2O2CR, primary alkylOR >> alkylO2CR. The reagent 1b, which has lower reactivity than 1a, may be advisable when higher selectivity is required, for example, synthesis of natural products. Additionally, TBDMS, TBDPS and PMB ethers are not affected by 1.2)
MOM = Methoxymethyl
MEM = 2-Methoxyethoxymethyl
Boc = tert-Butoxycarbonyl
Cbz = Benzyloxycarbonyl
TBDMS = tert-Butyldimethylsilyl
TBDPS = tert-Butyldiphenylsilyl
PMB = p-Methoxybenzyl
MEM = 2-Methoxyethoxymethyl
Boc = tert-Butoxycarbonyl
Cbz = Benzyloxycarbonyl
TBDMS = tert-Butyldimethylsilyl
TBDPS = tert-Butyldiphenylsilyl
PMB = p-Methoxybenzyl
References
- 1)Mild and selective reagents for cleavage of ether, ester, and carbamate protecting groups
- 2)Synthesis of prostaglandin F2α photoaffinity probes
- 3)Synthetic studies on spinosyn A.
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