tert-Butyldimethylsilyl ether (TBS, TBDMS)

Protection :
-
ReagentsTimeYield
-
Imidazole TBSCl5 min - 18 h88-98 %
-
Imidazole TBSCl20 min99 %Imidazole, TBSClCH2Cl2, DMFRT, 20 min, 99%
-
Imidazole TBSCl6 h - 5 d82-98 %
-
DMAP Imidazole TBSCl60 min - ON89-95 %
-
DMAP i-Pr2NEt TBSCl3 h88 %DMAP, i-Pr2NEt, TBSClCH2Cl20 °C to RT, 3 h, 88%"The following protection / deprotection sequence was due to a late deviation from the initial plan."
-
TBSCl60 min100 %TBSClCH2Cl2RT, 60 min, 100%
-
2,6-Lutidine TBSOTf15 - 60 min90-100 %
-
2,6-Lutidine DMAP TBSOTf4 h95 %2,6-Lutidine, DMAP, TBSOTfCH2Cl20 °C, 4 h, 95%
-
2,6-Lutidine TBSOTf60 min89 %2,6-Lutidine, TBSOTfMeCNRT, 60 min, 89%
-
DMAP Et3N TBSCl2.5 - 3 h69-71 %
-
DMAP TBSCl24 h71 %DMAP, TBSClPyrRT, 24 h, 71%
-
DMAP TBSCl N-Methylmorpholine30 min99 %DMAP, TBSCl, N-MethylmorpholineDMF0 °C to RT, 30 min, 99%
Deprotection :
-
ReagentsTimeYield
-
n-Bu4N+ F-15 min - 16 h70-100 %n-Bu4N+ F-THFRT, 105 min, 85%n-Bu4N+ F-THF0 °C, 15 min, 99%n-Bu4N+ F-THF50 °C, 16 h, 95%n-Bu4N+ F-THFRT, 7 h, 80%n-Bu4N+ F-THFRT, 8 h, 92%n-Bu4N+ F-THF50 °C, 60 min, 100%n-Bu4N+ F-THF70 °C, 4 h, 70%n-Bu4N+ F-THFRT, 3 h, 99%n-Bu4N+ F-THF0 °C, 3 h, 100%n-Bu4N+ F-THF0 °C to RT, 5 h, 97%n-Bu4N+ F-THFRT, ON, 83%n-Bu4N+ F-THF0 °C to RT, 3 h, 87%n-Bu4N+ F-THFRT, 4 h, 93%n-Bu4N+ F-THFRT, 60 min, 95%"The product is also obtained by the degradation of natural azadirachtin."n-Bu4N+ F-THFRT, 15 h, 97%
-
TASF15 min - 48 h80-94 %
-
HCl30 min - 6 h83-100 %
-
HCl30 min - ON83-99 %
-
Camphorsulfonic acid60 min90 %Camphorsulfonic acidMeOHRT, 60 min, 90%
-
Camphorsulfonic acid30 min97 %Camphorsulfonic acidCH2Cl2, MeOHRT, 30 min, 97%
-
Pyr.TsOHON93 %Pyr.TsOHEtOHRT, ON, 93%
-
BF3.OEt214 h89 %BF3.OEt2CH2Cl2RT, 14 h, 89%
-
Pyr.HF15 min - 3 h76-91 %
-
AcOH60 min100 %AcOHH2ORT, 60 min, 100%
-
LiBF431 h98 %LiBF4H2O, MeCN45-50 °C, 31 h, 98%
-
Pyr.HF34 h85 %Pyr.HFH2O, MeCNRT to 35 °C, 34 h, 85%
-
Et3NBn+ Cl- KF.2H2O10 h84 %Et3NBn+ Cl-, KF.2H2OMeCN60 °C, 10 h, 84%