Copolymers featuring pentafluorophenyl ester and photolabile amine units: synthesis and application as reactive photopatterns

2013 ◽  
Vol 4 (4) ◽  
pp. 891 ◽  
Author(s):  
Hui Zhao ◽  
Patrick Theato
2005 ◽  
Vol 117 (25) ◽  
pp. 3929-3932 ◽  
Author(s):  
Hiromasa Kurosaki ◽  
Yoshihiro Yamaguchi ◽  
Toshihiro Higashi ◽  
Kimitaka Soga ◽  
Satoshi Matsueda ◽  
...  

2011 ◽  
Vol 7 ◽  
pp. 1609-1619 ◽  
Author(s):  
Patrick Claude ◽  
Christian Lehmann ◽  
Thomas Ziegler

Phenyl 3,4,6-tri-O-benzyl-2-O-(3-carboxypropionyl)-1-thio-β-D-galactopyranoside (1) was condensed via its pentafluorophenyl ester 2 with 5-aminopentyl (4a), 4-aminobutyl (4b), 3-aminopropyl (4c) and 2-aminoethyl 4,6-O-benzylidene-β-D-glucopyranoside (4d), prepared from the corresponding N-Cbz protected glucosides 3a–d, to give the corresponding 2-[3-(alkylcarbamoyl)propionyl] tethered saccharides 5a–d. Intramolecular, ring closing glycosylation of the saccharides with NIS and TMSOTf afforded the tethered β(1→3) linked disaccharides 6a–c, the α(1→3) linked disaccharides 7a–d and the α(1→2) linked disaccharide 8d in ratios depending upon the ring size formed during glycosylation. No β(1→2) linked disaccharides were formed. Molecular modeling of saccharides 6–8 revealed that a strong aromatic stacking interaction between the aromatic parts of the benzyl and benzylidene protecting groups in the galactosyl and glucosyl moieties was mainly responsible for the observed regioselectivity and anomeric selectivity of the ring-closing glycosylation step.


2012 ◽  
Vol 13 (7) ◽  
pp. 2099-2109 ◽  
Author(s):  
Samantha McRae ◽  
Xiangji Chen ◽  
Katrina Kratz ◽  
Debasis Samanta ◽  
Elizabeth Henchey ◽  
...  

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