Matches in SemOpenAlex for { <https://semopenalex.org/work/W4236027730> ?p ?o ?g. }
Showing items 1 to 52 of
52
with 100 items per page.
- W4236027730 abstract "<p>The biological activity of azasugars has largely been attributed to their ability to mimic the oxocarbenium ion-like transition state formed during reactions with carbohydrate-processing enzymes and, for this reason, functional and stereochemical modifications of the azasugar scaffold have led to the development of specific and potent glycosidase inhibitors. Given the potential of azasugars as glycosidase inhibitors, we were interested in developing efficient methodology for their synthesis. This thesis highlights synthetic methodology developed to produce amino-imino-hexitols as azasugar scaffolds. Key in the synthesis of the amino-imino-hexitols was the application of a stereoselective Strecker reaction, without the need for chiral Lewis acids or catalysts, and an extension of an I2-mediated carbamate annulation to cyclise functionalised and protected alkenylamines. Sixteen amino-imino-hexitols were synthesized, including ten previously undisclosed substrates with the D-galacto, D-talo, and L-altro configurations. The novel amino-imino-hexitols were then tested for their ability to act as glycosidase inhibitors and substrates of the D-talo configuration showed promising inhibitory effects. Mechanistic considerations of the I2-mediated carbamate annulation are discussed and although the exact annulation mechanism has yet to be determined, experimental studies have revealed that an aziridine is not an intermediate in the reaction. Factors influencing the diastereoselectivity of the carbamate annulation are also explored. Furthermore, an in depth analysis of the high cis-selectivity of the carbamate annulation is investigated using density functional theory to calculate the transition states of iodocyclisations en route to the formation of carbamates. Taken as a whole, the applicability of the carbamate annulation to a variety of alkenylamines and an understanding of the factors controlling the diastereoselectivity of the reaction should make this methodology a valuable addition to the synthetic chemist’s toolbox.</p>" @default.
- W4236027730 created "2022-05-12" @default.
- W4236027730 creator A5010436531 @default.
- W4236027730 date "2021-11-12" @default.
- W4236027730 modified "2023-10-12" @default.
- W4236027730 title "The Synthesis of Azasugars Using an I2-mediated Carbamate Annulation" @default.
- W4236027730 doi "https://doi.org/10.26686/wgtn.17003287.v1" @default.
- W4236027730 hasPublicationYear "2021" @default.
- W4236027730 type Work @default.
- W4236027730 citedByCount "0" @default.
- W4236027730 crossrefType "dissertation" @default.
- W4236027730 hasAuthorship W4236027730A5010436531 @default.
- W4236027730 hasBestOaLocation W42360277301 @default.
- W4236027730 hasConcept C161790260 @default.
- W4236027730 hasConcept C178790620 @default.
- W4236027730 hasConcept C181199279 @default.
- W4236027730 hasConcept C181647583 @default.
- W4236027730 hasConcept C185592680 @default.
- W4236027730 hasConcept C196032511 @default.
- W4236027730 hasConcept C21951064 @default.
- W4236027730 hasConcept C2779303437 @default.
- W4236027730 hasConcept C59759590 @default.
- W4236027730 hasConcept C71240020 @default.
- W4236027730 hasConcept C7512685 @default.
- W4236027730 hasConceptScore W4236027730C161790260 @default.
- W4236027730 hasConceptScore W4236027730C178790620 @default.
- W4236027730 hasConceptScore W4236027730C181199279 @default.
- W4236027730 hasConceptScore W4236027730C181647583 @default.
- W4236027730 hasConceptScore W4236027730C185592680 @default.
- W4236027730 hasConceptScore W4236027730C196032511 @default.
- W4236027730 hasConceptScore W4236027730C21951064 @default.
- W4236027730 hasConceptScore W4236027730C2779303437 @default.
- W4236027730 hasConceptScore W4236027730C59759590 @default.
- W4236027730 hasConceptScore W4236027730C71240020 @default.
- W4236027730 hasConceptScore W4236027730C7512685 @default.
- W4236027730 hasLocation W42360277301 @default.
- W4236027730 hasLocation W42360277302 @default.
- W4236027730 hasOpenAccess W4236027730 @default.
- W4236027730 hasPrimaryLocation W42360277301 @default.
- W4236027730 hasRelatedWork W1787868692 @default.
- W4236027730 hasRelatedWork W1975336305 @default.
- W4236027730 hasRelatedWork W2002936227 @default.
- W4236027730 hasRelatedWork W2015097727 @default.
- W4236027730 hasRelatedWork W2746458387 @default.
- W4236027730 hasRelatedWork W2797107297 @default.
- W4236027730 hasRelatedWork W2945945418 @default.
- W4236027730 hasRelatedWork W2950553089 @default.
- W4236027730 hasRelatedWork W2951039223 @default.
- W4236027730 hasRelatedWork W3212804530 @default.
- W4236027730 isParatext "false" @default.
- W4236027730 isRetracted "false" @default.
- W4236027730 workType "dissertation" @default.