Abstract:
:The total synthesis of the sialic acid-containing antigenic epitope fucose GM(1) (Fuc-GM(1)) by an improved reactivity-based one-pot synthetic strategy is reported. Based on a thioglycoside reactivity database, three saccharide building blocks, 3, 4, and 5, were designed and prepared to incorporate a descending order of reactivity toward thiophilic activation. Using the reactivity-based one-pot synthetic method, the fully protected Fuc-GM(1) glycoside 2 was furnished in a facile manner, which was globally deprotected to give the Fuc-GM(1) glycoside 1. In addition, using the promoter system 1-(benzensulfinyl)piperidinetrifluoromethanesulfonic anhydride, the product yield was improved and the reaction time was reduced in comparison with the N-iodosuccinimidetrifluoromethanesulfonic acid- and dimethyl (thiomethyl) sulfonium trifluoromethanesulfonate-promoted systems.
journal_name
Proc Natl Acad Sci U S Aauthors
Mong TK,Lee HK,Duron SG,Wong CHdoi
10.1073/pnas.0337590100keywords:
subject
Has Abstractpub_date
2003-02-04 00:00:00pages
797-802issue
3eissn
0027-8424issn
1091-6490pii
0337590100journal_volume
100pub_type
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