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)228577 often sometimes avoid
t-butyldimethylsilyl (TBS or TBDMS)1615326 often sometimes avoid
benzyl1076215 often sometimes avoid
benzyloxycarbonyl (CBZ)776417 often sometimes avoid
acetyl686023 often sometimes avoid
p-methoxybenzyl (PMB)484719 often sometimes avoid
triisopropylsilyl (TIPS)344212 often sometimes avoid
methyl ester27177 often sometimes avoid
t-butyldiphenylsilyl (TBDPS)324015 often sometimes avoid
Trimethylsilane (TMS)374925 often sometimes avoid
9-fluorenyl methyloxycarbonyl (FMOC)403834 often sometimes avoid
2,2-dimethoxypropane1297 often sometimes avoid
1,3-dioxolane10117 often sometimes avoid
benzyl ether (OBn)1188 often sometimes avoid
CBZ330 often sometimes avoid
toluenesulfonyl ethyl ester402 often sometimes avoid
Trimethylsilane (TMS)331 often sometimes avoid
triethylsilyl (TES)4123 often sometimes avoid
fmoc121 often sometimes avoid
allyl ester9139 often sometimes avoid
t-butyl ester7147 often sometimes avoid
benzylidene101311 often sometimes avoid
isopropylidene91410 often sometimes avoid
Trichloroacetyl688 often sometimes avoid
dioxolane81010 often sometimes avoid
OTs328 often sometimes avoid
Trifluoroacetyl71313 often sometimes avoid
allyloxycarbonyl (alloc)91615 often sometimes avoid
DMAS2411 often sometimes avoid
trityl123521 often sometimes avoid
TEOC 2-(trimethylsilyl) ethoxycarbonyl51015 often sometimes avoid
pivaloyl153627 often sometimes avoid
TMSE 2 (trimethylsilyl) ethyl61419 often sometimes avoid
methoxymethyl (MOM)153931 often sometimes avoid
beta-methoxyethoxymethyl chloride6922 often sometimes avoid
trichloroethoxycarbonyl (Troc)92227 often sometimes avoid
tetrahydropyranyl (THP)253844 often sometimes avoid
methyl222642 often sometimes avoid
SEM 2 (trimethylsilyl) ethoxymethane122033 often sometimes avoid
2-naphthylmethyl (NAP)71332 often sometimes avoid
1,2 or 1,3 dithiane61033 often sometimes avoid
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