A MODEL REACTION FOR ASSESSING THE COUPLING AND CHIRAL EFFICIENCY OF REAGENTS IN DEPSIDE BOND FORMATION

Citation
Js. Davies et al., A MODEL REACTION FOR ASSESSING THE COUPLING AND CHIRAL EFFICIENCY OF REAGENTS IN DEPSIDE BOND FORMATION, Perkin transactions. 2, (12), 1995, pp. 2335-2339
Citations number
38
Categorie Soggetti
Chemistry Physical","Chemistry Inorganic & Nuclear
Journal title
ISSN journal
03009580
Issue
12
Year of publication
1995
Pages
2335 - 2339
Database
ISI
SICI code
0300-9580(1995):12<2335:AMRFAT>2.0.ZU;2-4
Abstract
The formation of Fmoc-L-Ala-L-Phlac-OBzl (and Fmoc-D-Ala-L-Phlac-OBzl if there is racemisation) has been monitored by HPLC analysis for a nu mber of coupling conditions between Fmoc-L-Ala-OH and H-Phlac-OBzl.dag ger For this depside link formation it is revealed that CDI, DCC/DMAP and mixed anhydride couplings gave yields near to 50%. Couplings via T BTU, TNTU and TSTU gave lower yields. The best yields were achieved by acid chloride (61%), urethane-N-carboxyanhydrides (80%) and by PyBroP coupling (82%).