Desert Island Protecting Groups

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	Use this often	Use this sometimes	Avoid using this		I use this...
t-butoxycarbonyl (BOC)	212	53	7	often	sometimes	avoid
t-butyldimethylsilyl (TBS or TBDMS)	156	49	25	often	sometimes	avoid
benzyl	101	59	15	often	sometimes	avoid
benzyloxycarbonyl (CBZ)	72	61	17	often	sometimes	avoid
acetyl	61	59	22	often	sometimes	avoid
p-methoxybenzyl (PMB)	44	45	19	often	sometimes	avoid
triisopropylsilyl (TIPS)	32	40	12	often	sometimes	avoid
methyl ester	24	15	7	often	sometimes	avoid
t-butyldiphenylsilyl (TBDPS)	31	37	15	often	sometimes	avoid
Trimethylsilane (TMS)	35	44	24	often	sometimes	avoid
9-fluorenyl methyloxycarbonyl (FMOC)	38	35	32	often	sometimes	avoid
1,3-dioxolane	10	9	7	often	sometimes	avoid
2,2-dimethoxypropane	9	8	7	often	sometimes	avoid
toluenesulfonyl ethyl ester	3	0	2	often	sometimes	avoid
Trimethylsilane (TMS)	2	3	1	often	sometimes	avoid
triethylsilyl (TES)	4	11	3	often	sometimes	avoid
fmoc	1	0	0	often	sometimes	avoid
allyl ester	9	10	9	often	sometimes	avoid
CBZ	0	2	0	often	sometimes	avoid
benzyl ether (OBn)	7	7	8	often	sometimes	avoid
t-butyl ester	6	13	7	often	sometimes	avoid
benzylidene	9	12	11	often	sometimes	avoid
Trichloroacetyl	5	7	7	often	sometimes	avoid
isopropylidene	7	14	10	often	sometimes	avoid
dioxolane	7	10	10	often	sometimes	avoid
Trifluoroacetyl	7	12	12	often	sometimes	avoid
allyloxycarbonyl (alloc)	9	15	14	often	sometimes	avoid
OTs	0	1	7	often	sometimes	avoid
DMAS	2	3	11	often	sometimes	avoid
TEOC 2-(trimethylsilyl) ethoxycarbonyl	5	9	15	often	sometimes	avoid
trityl	11	34	21	often	sometimes	avoid
pivaloyl	14	35	26	often	sometimes	avoid
TMSE 2 (trimethylsilyl) ethyl	6	13	19	often	sometimes	avoid
beta-methoxyethoxymethyl chloride	6	9	21	often	sometimes	avoid
methoxymethyl (MOM)	14	39	29	often	sometimes	avoid
trichloroethoxycarbonyl (Troc)	8	21	27	often	sometimes	avoid
methyl	22	25	42	often	sometimes	avoid
SEM 2 (trimethylsilyl) ethoxymethane	12	18	33	often	sometimes	avoid
tetrahydropyranyl (THP)	22	37	43	often	sometimes	avoid
2-naphthylmethyl (NAP)	7	12	31	often	sometimes	avoid
1,2 or 1,3 dithiane	6	10	31	often	sometimes	avoid

The Tour of Collective Wisdom presents:Desert Island Protecting Groups

The Tour of Collective Wisdom presents:
Desert Island Protecting Groups