212836-37-8Relevant academic research and scientific papers
Tetrabutylammonium nitrite - acetic anhydride system, tetrabutylammonium nitrite, tetrabutylammonium acetate, and cesium acetate - 18-crown-6 for efficient unmasking of alkyl N-phenylcarbamates
Akai, Shoji,Nishino, Noriaki,Iwata, Yukihiro,Hiyama, Jun-Ichi,Kawashima, Etsuko,Sato, Ken-Ichi,Ishido, Yoshiharu
, p. 5583 - 5586 (1998)
Novel unmasking procedures for alkyl N-phenylcarbamates are established by the use of a tetrabutylammonium nitrite (Bu4NNO2) - acetic anhydride system, Bu4NNO2, Bu4NOAc, and CsOAc 18-crown-6 towards variously functionalized sugar derivatives.
Selective deprotection method of N -phenylcarbamoyl group
Akai, Shoji,Tanaka, Rika,Hoshi, Hidekazu,Sato, Ken-Ichi
, p. 8802 - 8808 (2013/09/24)
We report an improved method for the selective deprotection of the N-phenylcarbamoyl group, which yields the corresponding alcohol without affecting other protecting groups. Deprotection was performed using di-tert-butyl dicarbonate and tetra-n-butylammon
Fluorous dimethylthiocarbamate (FDMTC) protecting groups for alcohols
Kojima, Masaru,Nakamura, Yutaka,Ishikawa, Takuma,Takeuchi, Seiji
, p. 6309 - 6314 (2007/10/03)
N,N-Bis(perfluoroalkyl)thiocarbamoyl chlorides (FDMTC-Cls) were synthesized as reagent for the protection of alcohols. Using the crystalline FDMTC-Cls, the FDMTC groups were introduced into the alcohol molecules in excellent yields in the presence of sodium hydride in THF at room temperature. The products were separated from the excess alcohols by solid-phase extraction with a fluorous reverse-phase silica gel column (Fluorous Solid Phase Extraction; FSPE). The FDMTC groups were readily removed by oxidation with m-chloroperbenzoic acid (m-CPBA) and subsequent hydrolysis with KHCO3.
