THE SOLID-PHASE SYNTHESIS OF N-ALKYLCARBAMATE OLIGOMERS

Citation
Sj. Paikoff et al., THE SOLID-PHASE SYNTHESIS OF N-ALKYLCARBAMATE OLIGOMERS, Tetrahedron letters, 37(32), 1996, pp. 5653-5656
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404039
Volume
37
Issue
32
Year of publication
1996
Pages
5653 - 5656
Database
ISI
SICI code
0040-4039(1996)37:32<5653:TSSONO>2.0.ZU;2-9
Abstract
An efficient method for the solid phase synthesis of N-alkylcarbamate oligomers from alternating carboxylic acid and N-alpha-Fmoc protected chiral p-nitrophenylcarbonate monomers has been developed. The general synthetic scheme involves four steps per coupling cycle: deprotection of the terminal amino group of the growing oligomer, acylation of the free amine with a carboxylic acid monomer, reduction of the resulting amide bond with borane and coupling of the secondary amine to a N-alp ha-Fmoc protected p-nitrophenyl carbonate monomer. This novel biopolym er which has two side chain residues per backbone carbamate linkage an d no backbone hydrogen bond donors may provide new frameworks for drug design as well as folded domains with novel physical and biological p roperties. Copyright (C) 1996 Elsevier Science Ltd