e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Acid-stable, solvolytically deblocked amino-protecting-groups applications of the 1, 3-dibromo-2-methyl-2-propyloxycarbonyl (DB-t-BOC) group

LA Carpino, NW Rice, EME Mansour…

Index: Carpino, Louis A.; Rice, Norman W.; Mansour, E. M. E.; Triolo, Salvatore A. Journal of Organic Chemistry, 1984 , vol. 49, # 5 p. 836 - 842

Full Text: HTML

Citation Number: 16

Abstract

The effects of structure on the ease of solvolytic deblocking of an array of cy-halo-tert-alkyl carbamates 1 have been studied. The corresponding thiolcarbamates were shown to undergo isomerization and other reactions due to participation of the sulfur atom. 1, 1, 1, 3, 3, 3-Hexachloro-2-(bromomethyl)-2-propyl carbamates were relatively unreactive toward solvolytic deblocking. On the other hand the 1, 3-dibromo-2-methyl-2-propyloxycarbonyl ...

(1-bromo-2-methylbutan-2-yl) carbonochloridate Structure

(1-bromo-2-meth...

Cyclohexylamine Structure

Cyclohexylamine

~62%

(1-bromo-2-methylbutan-2-yl) N-cyclohexylcarbamate Structure

(1-bromo-2-meth...

1-bromo-2-methyl-butan-2-ol Structure

1-bromo-2-methy...

~%

(1-bromo-2-methylbutan-2-yl) N-cyclohexylcarbamate Structure

(1-bromo-2-meth...

3-Bromo-2-methylpropene Structure

3-Bromo-2-methy...

~83%

1,3-dibromo-2-methylpropan-2-ol Structure

1,3-dibromo-2-m...

phosgene Structure

1,3-dibromo-2-methylpropan-2-ol Structure

1,3-dibromo-2-m...

~85%

(1,3-dibromo-2-methylpropan-2-yl) carbonochloridate Structure

(1,3-dibromo-2-...

(1-bromo-2,3-dimethylbutan-2-yl) carbonochloridate Structure

(1-bromo-2,3-di...

Structure

~66%

1-bromo-2,3-dimethylbutan-2-ol,phenylcarbamic acid Structure

1-bromo-2,3-dim...

1-bromo-2,3-dimethyl-butan-2-ol Structure

1-bromo-2,3-dim...

~%

1-bromo-2,3-dimethylbutan-2-ol,phenylcarbamic acid Structure

1-bromo-2,3-dim...

1-bromo-2,3-dimethyl-butan-2-ol Structure

1-bromo-2,3-dim...

~%

(1-bromo-2,3-dimethylbutan-2-yl) N-cyclohexylcarbamate Structure

(1-bromo-2,3-di...

(1-bromo-2,3-dimethylbutan-2-yl) carbonochloridate Structure

(1-bromo-2,3-di...

Cyclohexylamine Structure

Cyclohexylamine

~35%

(1-bromo-2,3-dimethylbutan-2-yl) N-cyclohexylcarbamate Structure

(1-bromo-2,3-di...

(1,3-dibromo-2-methylpropan-2-yl) carbonochloridate Structure

(1,3-dibromo-2-...

Structure

~45%

1,3-dibromo-2-methylpropan-2-ol,phenylcarbamic acid Structure

1,3-dibromo-2-m...

phosgene Structure

Cyclohexanol,1-(bromomethyl)- Structure

Cyclohexanol,1-...

~64%

[1-(bromomethyl)cyclohexyl] carbonochloridate Structure

[1-(bromomethyl...

3-(bromomethyl)pentan-3-yl carbonochloridate Structure

3-(bromomethyl)...

Structure

~48%

3-(bromomethyl)pentan-3-ol,phenylcarbamic acid Structure

3-(bromomethyl)...

3-bromomethyl-pentan-3-ol Structure

3-bromomethyl-p...

~%

3-(bromomethyl)pentan-3-ol,phenylcarbamic acid Structure

3-(bromomethyl)...

3-(bromomethyl)pentan-3-yl carbonochloridate Structure

3-(bromomethyl)...

Cyclohexylamine Structure

Cyclohexylamine

~70%

3-(bromomethyl)pentan-3-yl N-cyclohexylcarbamate Structure

3-(bromomethyl)...

3-bromomethyl-pentan-3-ol Structure

3-bromomethyl-p...

~%

3-(bromomethyl)pentan-3-yl N-cyclohexylcarbamate Structure

3-(bromomethyl)...

1,1-bis(trichloromethyl)ethylene oxide Structure

1,1-bis(trichlo...

~87%

2-(bromomethyl)-1,1,1,3,3,3-hexachloropropan-2-ol Structure

2-(bromomethyl)...

phosgene Structure

1-bromo-2-methyl-butan-2-ol Structure

1-bromo-2-methy...

~56%

(1-bromo-2-methylbutan-2-yl) carbonochloridate Structure

(1-bromo-2-meth...

phosgene Structure

1-bromo-2,3-dimethyl-butan-2-ol Structure

1-bromo-2,3-dim...

~62%

(1-bromo-2,3-dimethylbutan-2-yl) carbonochloridate Structure

(1-bromo-2,3-di...

[1-(bromomethyl)cyclohexyl] carbonochloridate Structure

[1-(bromomethyl...

Structure

~81%

1-(bromomethyl)cyclohexan-1-ol,phenylcarbamic acid Structure

1-(bromomethyl)...

Cyclohexanol,1-(bromomethyl)- Structure

Cyclohexanol,1-...

~%

1-(bromomethyl)cyclohexan-1-ol,phenylcarbamic acid Structure

1-(bromomethyl)...

2,2-Dimethylthiirane Structure

2,2-Dimethylthiirane

phosgene Structure

Structure

~%

S-(2-bromo-2-methylpropyl) N-phenylcarbamothioate Structure

S-(2-bromo-2-me...

phosgene Structure

3-bromomethyl-pentan-3-ol Structure

3-bromomethyl-p...

~20%

3-(bromomethyl)pentan-3-yl carbonochloridate Structure

3-(bromomethyl)...

(1-bromo-2-methylbutan-2-yl) carbonochloridate Structure

(1-bromo-2-meth...

Structure

~46%

1-bromo-2-methylbutan-2-ol,phenylcarbamic acid Structure

1-bromo-2-methy...

1-bromo-2-methyl-butan-2-ol Structure

1-bromo-2-methy...

~%

1-bromo-2-methylbutan-2-ol,phenylcarbamic acid Structure

1-bromo-2-methy...

2,2-Dimethylthiirane Structure

2,2-Dimethylthiirane

phosgene Structure

Structure

~%

S-(2-chloro-2-methylpropyl) N-phenylcarbamothioate Structure

S-(2-chloro-2-m...

Detail

2,2-Dimethylthiirane Structure

2,2-Dimethylthiirane

phosgene Structure

Structure

~%

S-(2-chloro-2-methylpropyl) N-phenylcarbamothioate Structure

S-(2-chloro-2-m...

2,2-Dimethylthiirane Structure

2,2-Dimethylthiirane

phosgene Structure

Structure

~%

S-(2-chloro-2-methylpropyl) N-phenylcarbamothioate Structure

S-(2-chloro-2-m...

Detail

2-(bromomethyl)-1,1,1,3,3,3-hexachloropropan-2-yl carbonochloridate Structure

2-(bromomethyl)...

Structure

~89%

2-(bromomethyl)-1,1,1,3,3,3-hexachloropropan-2-ol,phenylcarbamic acid Structure

2-(bromomethyl)...