(Acyloxy)alkoxy moiety as amino acids protecting group for the synthesis of (R,R)-2,7 diaminosuberic acid via RCM.
A new synthetic pathway is described to prepare asymmetrically protected 2,7-diaminosuberic acid. This strategy exploits (acyloxy)alkoxy promoiety as protecting group and RCM reaction using second generation Grubbs catalyst and provides the trans isomer of (2R,7R)-7-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-(tert-butoxycarbonylamino)-8- methoxy-8-oxooct-4-enoic acid, which was in turn reduced to obtain (2R,7R)-7-(((9H-fluoren-9-yl)methoxy)carbonylamino)- 2-(tert-butoxycarbonylamino)-8-methoxy-8-oxooctanoic acid.
Faculty of Pharmacy, Department of Pharmaceutical Sciences, University of Chieti-Pescara G. d' Annunzio, Chieti, Italy. a.mollica@unich.it
Adriano
A
Mollica
Federica
F
Feliciani
Azzurra
A
Stefanucci
Evgeny A
EA
Fadeev
Francesco
F
Pinnen
D000438:Alcohols / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D055598:Chemical Phenomena; D003960:Diaminopimelic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
C437390:2,7-diaminosuberic acid; D000438:Alcohols; D000596:Amino Acids; C059688:alkoxyl radical; D003960:Diaminopimelic Acid