The Tour of Collective Wisdom presents:
Desert Island Protecting Groups


Choosing a good protecting group for your molecule can save a lot of time. The choices, however, are often overwhelming (T. Green, Protecting Groups in Organic Synthesis). Protecting groups are listed below in order of popularity.

Protecting group:
I often use this I sometimes use this I avoid this
Verification:
Protecting group Use this often Use this sometimes Avoid using this I use this...
t-butoxycarbonyl (BOC)226577 often sometimes avoid
t-butyldimethylsilyl (TBS or TBDMS)1615325 often sometimes avoid
benzyl1066215 often sometimes avoid
benzyloxycarbonyl (CBZ)766417 often sometimes avoid
acetyl676023 often sometimes avoid
p-methoxybenzyl (PMB)474719 often sometimes avoid
triisopropylsilyl (TIPS)344212 often sometimes avoid
methyl ester26177 often sometimes avoid
t-butyldiphenylsilyl (TBDPS)314015 often sometimes avoid
Trimethylsilane (TMS)374924 often sometimes avoid
9-fluorenyl methyloxycarbonyl (FMOC)403833 often sometimes avoid
2,2-dimethoxypropane1197 often sometimes avoid
1,3-dioxolane10117 often sometimes avoid
toluenesulfonyl ethyl ester402 often sometimes avoid
Trimethylsilane (TMS)331 often sometimes avoid
benzyl ether (OBn)1088 often sometimes avoid
CBZ230 often sometimes avoid
triethylsilyl (TES)4123 often sometimes avoid
fmoc120 often sometimes avoid
allyl ester9129 often sometimes avoid
t-butyl ester7137 often sometimes avoid
Trichloroacetyl687 often sometimes avoid
benzylidene91311 often sometimes avoid
isopropylidene81410 often sometimes avoid
dioxolane81010 often sometimes avoid
OTs327 often sometimes avoid
Trifluoroacetyl71312 often sometimes avoid
allyloxycarbonyl (alloc)91515 often sometimes avoid
DMAS2411 often sometimes avoid
trityl123521 often sometimes avoid
TEOC 2-(trimethylsilyl) ethoxycarbonyl51015 often sometimes avoid
pivaloyl153626 often sometimes avoid
TMSE 2 (trimethylsilyl) ethyl61419 often sometimes avoid
methoxymethyl (MOM)153930 often sometimes avoid
beta-methoxyethoxymethyl chloride6922 often sometimes avoid
tetrahydropyranyl (THP)253843 often sometimes avoid
trichloroethoxycarbonyl (Troc)82227 often sometimes avoid
methyl222642 often sometimes avoid
SEM 2 (trimethylsilyl) ethoxymethane122033 often sometimes avoid
2-naphthylmethyl (NAP)71232 often sometimes avoid
1,2 or 1,3 dithiane61032 often sometimes avoid
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