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Title: Solid-phase synthesis of purine derivatives
Authors: FU HAN
Keywords: solid-phase synthesis, purine, traceless linker, resin, cleavage, regioselective
Issue Date: 19-Jan-2007
Citation: FU HAN (2007-01-19). Solid-phase synthesis of purine derivatives. ScholarBank@NUS Repository.
Abstract: This thesis reports the development of novel methodologies for the solid phase synthesis (SPS) of purine derivatives. The first project involves the SPS of 2,9-disubstituted-6-oxopurines using Wang resin. The synthetic strategy was designed to load the 6-chloropurine scaffold directly onto the solid support via an ether linker. After combinatorial modifications at N9 and C2, the resin was cleaved and 2,9-disubstituted-6-oxopurines were released. The second project focuses on the investigation of the regioselective SPS of N7-substituted purine using REM resin. The synthetic strategy was devised to anchor the REM resin at N9 of 6-chloropurine, leaving N7 as the steric priority for alkylation. Further modification at N1 followed by cleavage resulted in 1,7-disubstituted-6-oxopurines being obtained.The third project centers on widening the SPS of purines based on the purine ring formation strategy. The synthetic strategy was designed to load the 5-amino-4,6-dichloropyrimidine onto BOBA resin to construct the diamine key intermediate. Using this intermediate, various substituted purines including 1,7,8-trisubstituted purines, 8-unsubstituted purines, 8-azapurines and [i]-condensed purines could be prepared.
Appears in Collections:Ph.D Theses (Open)

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