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2007:
Tony Kurissery A; Denton Richard W; Dilhas Anna; Jiménez-Barbero Jesús; Mootoo David R
Synthesis of beta-C-galacto-pyranosides with fluorine on the pseudoanomeric substituent.
Organic letters 2007;
9(
8):.
[reaction: see text] beta-C-galacto-Pyranosides with CHF and CF2 substitutes for the glycosidic oxygen were prepared through a four-step sequence starting from a central 1-thio-1,2-O-isopropylidene acetal alcohol and different alpha-fluoro- and alpha,alpha-difluoro acids. The key step in the synthesis is the oxocarbenium cyclization of an intermediate enol ether-thioacetal to a C1-substituted glycal.
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