107897-41-6

Upstream product

• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 29681-57-0 tert-butyldimethylsilane 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 

Downstream Products

• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 

Relevant academic research and scientific papers

Catalytic dehydrogenative N-((triisopropylsilyl)oxy)carbonyl (Tsoc) protection of amines using iPr3SiH and CO2

A versatile method has been found to catalyze the dehydrogenative N-((triisopropylsilyl)oxy)carbonyl (Tsoc) protection of amines using Pd/C, volatile iPr3SiH and CO2 gas without the liberation of any salts. A simple filtration/evaporation process facilitates the easy isolation of the product, thereby enhancing the utility of Tsoc as an amine-protecting group in organic synthesis.

Syntheses and Reactions of Silyl Carbamates. 1. Chemoselective Transformation of Amino Protecting Groups via tert-Butyldimethylsilyl Carbamates

The N-tert-butyldimethylsilyloxycarbonyl group (silyl carbamate) was synthesized from commonly used amino protecting groups such as N-tert-butoxycarbonyl (Boc) and N-benzyloxycarbonyl (Z) by treatment with tert-butyldimethylsilyl trifluoromethanesulfonate/2,6-lutidine and tert-butyldimethylsilane/Pd(OAc)2, respectively.This novel species, upon activation with fluoride ion, reacts with a variety of electrophiles to give N-ester type compounds in high yield.For example, the conversion of N-t-Boc compounds into their corresponding N-Z compounds via a silyl carbamate was accomplished under these mild reaction conditions.