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Synfacts 2023; 19(02): 0209
DOI: 10.1055/s-0042-1753215
Peptide Chemistry

Chemoselective Cleavage of the tert-Butoxycarbonyl Group from Di-tert-butylimidodicarbonate

Contributor(s):
Hisashi Yamamoto
,
Isai Ramakrishna
Yadav JS, Reddy BV. S, Reddy KS, Reddy KB. Indian Institute of Chemical Technology, Hyderabad, India
Indium-Mediated Facile Cleavage of the t-Butoxycarbonyl Group from Di-t-butylimidodicarbonate.

Tetrahedron Lett. 2002;
43: 1549-1551
DOI: 10.1016/S0040-4039(01)02374-7.
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Key words

zinc - indium - di-tert-butylimidodicarbonate

Significance

Chemoselective reactions play a vital role in organic synthesis. Chemoselective protection and deprotection with protecting groups is one of the most important technologies in peptide chemistry. In 2002, Yadav and coworkers developed the facile Zn/In-mediated cleavage of the tert-butoxycarbonyl group from di-tert-butylimidodicarbonate.


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Comment

Indium- or zinc-mediated chemoselective deprotection of the tert-butoxycarbonyl group from di-tert-butylimidodicarbonate proceeded smoothly to deliver the desired mono-Boc-protected amines in high yields. This protocol is highly chemoselective, practically simple, mild, and efficient for various amino acids.


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Publication History

Article published online:
17 January 2023

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