Browsing by Author "Lico, Larry S."

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Synthesis of a fluorogenic substrate for alpha-L-iduronidase
(2013)
Lu, Fu-Chieh
;
Lico, Larry S.
;
Hung, Shang-Cheng
;
應用化學系
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Department of Applied Chemistry
An alternative reaction pathway towards the preparation of an L-idopyranose derivative and its application to the synthesis of the alpha-L-iduronidase fluorogenic substrate 4-methylcoumarin-7-yl-alpha-L-iduronic acid as well as its 3-undecyl derivative are described. The L-ido sugar was prepared by converting the commercially available diacetone-alpha-D-glucose to methyl 1,2,3,4-tetra-O-acetyl-L-idopyranuronate via oxidation, esterification, and regioselective acetylation of the key intermediate 1,2:3,5-di-O-isopropylidene-beta-L-idofuranose. Mitsunobu-type glycosylation was employed in the coupling of the L-ido donor with the 4-methylcoumarin acceptors. This newly developed route reduced the difficulties previously encountered in the synthesis of the alpha-L-iduronidase fluorogenic substrate.
Synthesis of a Furanosyl-pyranone Derivative Related to the Tri-O-heterocyclic Core of Herbicidins
(2012-03-01)
Hsu, Ching-Yun
;
Lee, I-Chi
;
Lico, Larry S.
;
Uang, Biing-Jiun
;
Hung, Shang-Cheng
A new compound that is structurally related to the undecose ring structure of herbicidins has been prepared. The synthesis of this novel furanosyl-pyranone derivative was made possible through the regioselective reductive ring-opening of a 3,5-O-benzylidene-D-xylofuranose and the hetero-Diels-Alder reaction of an aldehyde and a Danishefsky-type diene. The highly functionalized pyranone derivative can be a useful precursor for the synthesis of herbicidins.