134149-47-6Relevant articles and documents
Anomeric alkylations and acylations of unprotected mono- and disaccharides mediated by pyridoneimine in aqueous solutions
Dey, Kalyan,Jayaraman, Narayanaswamy
supporting information, p. 2224 - 2227 (2022/02/17)
A site-specific deprotonation followed by alkylations and acylations of sugar hemiacetals to the corresponding alkyl glycosides and acylated sugars in aqueous solutions is disclosed herein. Pyridoneimine as a new base is developed to mediate the deprotonation of readily available sugar hemiacetals and further reactions with alkylation and acylation agents.
Synthesis of the spirastrellolide A, B/C spiroketal: Enabling solutions for problematic au(I)-catalyzed spiroketalizations
Butler, Barry B.,Manda, Jagadeesh Nagendra,Aponick, Aaron
supporting information, p. 1902 - 1905 (2015/04/27)
A synthesis of the spirastrellolide A, B/C-ring monounsaturated spiroketal is reported. The key step relies on a Au-catalyzed spiroketalization of a propargyl triol employing an acetonide as a regioselectivity regulator. Through observation and analysis, a set of conditions has been developed that facilitates the use of a mixture of diastereomeric substrates, obviating the need to control the stereochemistry of the propargyl stereocenter and enabling a convenient retrosynthetic disconnection. The key reaction proceeds in 80% yield in 1 min at ambient temperature with the Me3PAuCl/AgOTf catalyst system. These conditions should be widely applicable for new synthetic endeavors as they appear to overcome all issues with the Au-catalyzed spiroketalization.
Green glycosylation promoted by reusable biomass carbonaceous solid acid: An easy access to β-stereoselective terpene galactosides
Gorityala, Bala Kishan,Ma, Jimei,Pasunooti, Kalyan Kumar,Cai, Shuting,Liu, Xue-Wei
supporting information; experimental part, p. 573 - 577 (2011/05/06)
An efficient green protocol has been developed for the atom economic glycosylation of unprotected, unactivated glycosyl donors and glycosylation of glycosyl trichloroacetimidates with the aid of reusable eco-friendly biomass carbonaceous solid acid as catalyst. The Royal Society of Chemistry.