Acidic and basic deprotection strategies of borane-protected phosphinothioesters for the traceless Staudinger ligation.
The traceless Staudinger ligation has recently found various applications in the field of peptide synthesis and modification, including immobilization and cyclization strategies. In this report, we utilize the traceless Staudinger ligation in the formation of amide bonds, which allows the acquisition of acylated aminosugars and peptides as well as the cyclization of peptides. A key element in these synthetic procedures is the use of a borane-protected phosphinomethanethiol, which is demonstrated to be prone towards oxidation in its unprotected form, during the synthesis of phosphinothioesters. In combination with acidic and basic deprotection strategies for the borane-protected phosphinothioesters, amide bonds can be formed in the presence of azides in moderate to good overall yields.
Mühlberg
Michaela
M
Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany.
Jaradat
Da'san M M
DM
Kleineweischede
Rolf
R
Papp
Ilona
I
Dechtrirat
Decha
D
Muth
Silvia
S
Broncel
Malgorzata
M
Hackenberger
Christian P R
CP
D000577:Amides; D000606:Amino Sugars / Q000138:chemical synthesis*; D001386:Azides; D001880:Boranes / Q000737:chemistry*; D004952:Esters; D055601:Organic Chemistry Phenomena; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis*; D013457:Sulfur Compounds / Q000138:chemical synthesis / Q000737:chemistry*
D000577:Amides; D000606:Amino Sugars; D001386:Azides; D001880:Boranes; D004952:Esters; D063065:Organophosphonates; D010455:Peptides; D013457:Sulfur Compounds; C509588:phosphinothioic acid