Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

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Chemical Compound Review:

AG-F-24450 trifluoro- (trifluoromethylsulfonyloxysul fo...

Synonyms: CHEBI:48509, AC1Q4KIW, AC1Q6YDX, LS-192058, AKOS007930319, ...

Kanekiyo, N. et al., Crich, D. et al., Crich, D. et al.

Crich, Banerjee, Crich, Vinogradova,

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High impact information on trifluoro-triflyloxysulfonyl-methane

In glycosylations carried out with preactivation with the 1-benzenesulfinylpiperidine/trifluoromethanesulfonic anhydride couple, both the D- and L-glycero series exhibit excellent beta-selectivity with a range of glycosyl acceptors [1].
The two key steps involved are (1) a thermal electrocyclic reaction of the 3-alkenylindole-2-aldoxime 10 and (2) a thermal cyclization of 3-alkynylindole-2-aldoxime 11 to construct the beta-carboline N-oxides 8, which upon heating with acetic anhydride and sequential treatment with trifluoromethanesulfonic anhydride gave the triflates 18 [2].

Associations of trifluoro-triflyloxysulfonyl-methane with other chemical compounds

The synthesis of 4,6-O-benzylidene-protected 2-deoxyarabino-, 3-deoxyarabino-, and 3-deoxyribothioglycosides is described and their glycosylation reactions, with activation by either 1-benzenesulfinyl piperidine/trifluoromethansulfonic anhydride or diphenyl sulfoxide/trifluoromethanesulfonic anhydride, studied [3].

References

Stereocontrolled synthesis of the D- and L-glycero-beta-D-manno-heptopyranosides and their 6-deoxy analogues. Synthesis of methyl alpha-l-rhamno-pyranosyl-(1-->3)-D-glycero-beta-D-manno-heptopyranosyl- (1-->3)-6-deoxy-glycero-beta-D-manno-heptopyranosyl-(1-->4)-alpha-L- rhamno-pyranoside, a tetrasaccharide subunit of the lipopolysaccharide from Plesimonas shigelloides. Crich, D., Banerjee, A. J. Am. Chem. Soc. (2006) [Pubmed]
Total syntheses of beta-carboline alkaloids, (R)-(-)-pyridindolol K1, (R)-(-)-pyridindolol K2, and (R)-(-)-pyridindolol. Kanekiyo, N., Kuwada, T., Choshi, T., Nobuhiro, J., Hibino, S. J. Org. Chem. (2001) [Pubmed]
On the Influence of the C2-O2 and C3-O3 Bonds in 4,6-O-Benzylidene-Directed beta-Mannopyranosylation and alpha-Glucopyranosylation. Crich, D., Vinogradova, O. J. Org. Chem. (2006) [Pubmed]

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