- Controllable Activation of Pd-G3 Palladacycle Precatalyst in the Presence of Thiosugars: Rapid Access to 1-Aminobiphenyl Thioglycoside Atropoisomers at Room Temperature
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A controllable method for the functionalization of XantPhos Pd-G3 precatalyst with thiosugars and thiols has been established. Under mild and operationally simple reaction conditions through just mixing of precatalyst and thiosugars (α- or β-mono-, di- and poly-thiosugar derivatives) in water at 25 °C for 20 min, a series of 1-aminobiphenyl thioglycosides that are difficult to synthesize by classical methods has been synthesized in very high yields.
- AL-Shuaeeb, Riyadh Ahmed Atto,Dejean, Camille,Alami, Mouad,Messaoudi, Samir
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supporting information
p. 3114 - 3118
(2017/12/26)
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- Glycosylated eumelanin building blocks by thioglycosylation of 5,6-diacetoxyindole with an expedient selenium-based dynamic-mixture methodology
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A series of 3-thioglycosylated 5,6-diacetoxyindole derivatives, which are important tools for eumelanin research and application, were prepared through a practical and efficient approach exploiting a dynamic mixture of thioglycoside agents. The strategy is feasible for installing both mono- and disaccharide units and relies on the facile in situ conversion of glycosyl disulfides into the corresponding, more reactive, phenylselenenyl sulfides in the presence of diphenyl diselenide, N-bromosuccinimide (NBS) and tetrabutylammonium bromide (TBAB). An expedient thioglycosidation of 5,6-diacetoxyindole with a dynamic mixture of thioglycosides is described. Copyright
- Adinolfi, Matteo,D'Ischia, Marco,Iadonisi, Alfonso,Leone, Loredana,Pezzella, Alessandro,Valerio, Silvia
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experimental part
p. 4333 - 4338
(2012/09/22)
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- Free-radical hydrothiolation of glycals: A thiol-ene-based synthesis of S-disaccharides
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A method for the synthesis of a new family of 1-deoxy S-disaccharides has been established via free-radical hydrothiolation of glycals by sugar thiols (thiol-ene coupling). The photoinduced coupling between four tri-O-acetyl-d-glycals and three different sugar thiols reveals that the reaction efficiency and stereoselectivity are highly dependent on the stereochemistry of the OAc groups at C3 and C4 of the glycal.
- Staderini, Samuele,Chambery, Angela,Marra, Alberto,Dondoni, Alessandro
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supporting information; experimental part
p. 702 - 704
(2012/02/15)
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