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)	157	39	5	often	sometimes	avoid
t-butyldimethylsilyl (TBS or TBDMS)	138	37	21	often	sometimes	avoid
benzyl	72	43	8	often	sometimes	avoid
acetyl	55	47	16	often	sometimes	avoid
benzyloxycarbonyl (CBZ)	49	44	13	often	sometimes	avoid
p-methoxybenzyl (PMB)	39	36	14	often	sometimes	avoid
triisopropylsilyl (TIPS)	26	29	8	often	sometimes	avoid
t-butyldiphenylsilyl (TBDPS)	26	26	9	often	sometimes	avoid
methyl ester	14	6	3	often	sometimes	avoid
Trimethylsilane (TMS)	28	34	18	often	sometimes	avoid
9-fluorenyl methyloxycarbonyl (FMOC)	29	26	20	often	sometimes	avoid
t-butyldimethylsilyl (TBS or TBDMS)	5	3	0	often	sometimes	avoid
t-butoxycarbonyl (BOC)	5	0	0	often	sometimes	avoid
1,3-dioxolane	7	5	3	often	sometimes	avoid
benzyl	4	1	0	often	sometimes	avoid
benzyl ether (OBn)	4	0	0	often	sometimes	avoid
allyl ester	5	7	3	often	sometimes	avoid
Trifluoroacetyl	5	7	3	often	sometimes	avoid
cbz	2	4	0	often	sometimes	avoid
Trichloroacetyl	4	5	3	often	sometimes	avoid
triethylsilyl (TES)	2	6	1	often	sometimes	avoid
2,2-dimethoxypropane	5	5	4	often	sometimes	avoid
dioxolane	6	5	6	often	sometimes	avoid
pmbs	0	2	0	often	sometimes	avoid
t-butyl ester	5	7	5	often	sometimes	avoid
benzylidene	7	10	8	often	sometimes	avoid
DMAS	1	2	4	often	sometimes	avoid
isopropylidene	5	13	8	often	sometimes	avoid
TEOC 2-(trimethylsilyl) ethoxycarbonyl	2	9	7	often	sometimes	avoid
allyloxycarbonyl (alloc)	7	9	13	often	sometimes	avoid
pivaloyl	12	33	19	often	sometimes	avoid
trityl	9	29	16	often	sometimes	avoid
beta-methoxyethoxymethyl chloride	5	8	15	often	sometimes	avoid
TMSE 2 (trimethylsilyl) ethyl	3	11	15	often	sometimes	avoid
methoxymethyl (MOM)	11	32	24	often	sometimes	avoid
trichloroethoxycarbonyl (Troc)	7	20	20	often	sometimes	avoid
1,2 or 1,3 dithiane	5	10	20	often	sometimes	avoid
SEM 2 (trimethylsilyl) ethoxymethane	11	14	28	often	sometimes	avoid
tetrahydropyranyl (THP)	13	32	32	often	sometimes	avoid
2-naphthylmethyl (NAP)	4	11	25	often	sometimes	avoid
methyl	17	22	39	often	sometimes	avoid

The Tour of Collective Wisdom presents:Desert Island Protecting Groups

The Tour of Collective Wisdom presents:
Desert Island Protecting Groups