82819-30-5Relevant academic research and scientific papers
MW-enhanced high-speed deprotection of Boc group using p-TsOH and concommitant formation of N-Me-amino acid benzyl ester p-TsOH salts
Suresh Babu, Vommina V.,Patil, Basanagoud S.,Vasanthakumar, Ganga-Ramu
, p. 1795 - 1802 (2007/10/03)
A high-speed, complete deprotection of Boc group from Boc amino acids and protected peptide esters employing p-TsOH in toluene under microwave irradiation is found to be complete in 30s. The deprotection can be carried out in methanol and acetonitrile also. Under the present conditions, C-peptide benzyl esters and O-benzyl ethers have been found to be stable. This has permitted us to carry out the synthesis of [Leu]enkephalin employing the Boc/Bzl-group strategy. Further more, it has been found that both Nα-Fmoc and N α-Z groups are completely stable. The present conditions can be extended for the concomitant removal of the Boc group and the formation of C-benzyl amino acid esters as well. This has been utilized for the synthesis of N-Me amino acid benzyl esters starting from Boc-N-Me amino acids in a single step. Copyright Taylor & Francis, Inc.
