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Named reactions

Get references and more from over 229 named organic chemical reaction

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Protecting Groups

Get the conditions needed to install/remove a wide range of protecting groups.

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Search synthesis

tert-Butyldimethylsilyl ether (TBS, TBDMS)

Protection

 
Reagents
Solvents
Temperature
Time
Yield
TBSCl, Imidazole
CH2Cl2
RT
5 min - 18 h
88-98 %
TBSCl, Imidazole
CH2Cl2, DMF
RT
20 min
99 %
TBSCl, Imidazole
DMF
0 °C - RT
6 h - 5 d
82-98 %
TBSCl, Imidazole, DMAP
CH2Cl2
0 °C - RT
60 min - ON
89-95 %
TBSCl, i-Pr2NEt, DMAP
CH2Cl2
0 °C - RT
3 h
88 %
TBSCl
CH2Cl2
RT
60 min
100 %
TBSOTf, 2,6-Lutidine
CH2Cl2
0 °C
15 - 60 min
90-100 %
TBSOTf, 2,6-Lutidine, DMAP
CH2Cl2
0 °C
4 h
95 %
TBSOTf, 2,6-Lutidine
MeCN
RT
60 min
89 %
TBSCl, Et3N, DMAP
DMF
-20 °C - RT
2.5 - 3 h
69-71 %
TBSCl, DMAP
Pyr
RT
24 h
71 %
TBSCl, DMAP, N-Methylmorpholine
DMF
0 °C - RT
30 min
99 %

Deprotection

 
Reagents
Solvents
Temperature
Time
Yield
n-Bu4N+ F-
THF
0 - 70 °C
15 min - 16 h
70-100 %
TASF
THF
RT
15 min - 48 h
80-94 %
HCl
THF, H2O
0 °C - RT
30 min - 6 h
83-100 %
HCl
MeOH, H2O
0 °C - RT
30 min - ON
83-99 %
Camphorsulfonic acid
MeOH
RT
60 min
90 %
Camphorsulfonic acid
MeOH, CH2Cl2
RT
30 min
97 %
Pyr.TsOH
EtOH
RT
ON
93 %
BF3.OEt2
CH2Cl2
RT
14 h
89 %
Pyr.HF
THF
RT
15 min - 3 h
76-91 %
AcOH
H2O
RT
60 min
100 %
LiBF4
MeCN, H2O
45-50 °C
31 h
98 %
Pyr.HF
MeCN, H2O
RT - 35 °C
34 h
85 %
KF.2H2O, Et3NBn+ Cl-
MeCN
60 °C
10 h
84 %
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