5517-61-3Relevant articles and documents
Site-Selective and Stereoselective C-H Alkylations of Carbohydrates via Combined Diarylborinic Acid and Photoredox Catalysis
Dimakos, Victoria,Su, Hsin Y.,Garrett, Graham E.,Taylor, Mark S.
, p. 5149 - 5153 (2019)
Diphenylborinic acid serves as a cocatalyst for site- and stereoselective C-H alkylation reactions of carbohydrates under photoredox conditions using quinuclidine as the hydrogen atom transfer mediator. Products arising from selective abstraction of the equatorial hydrogens of cis-1,2-diol moieties, followed by C-C bond formation with net retention of configuration, are obtained. Computational modeling supports a mechanism involving formation of a tetracoordinate borinic ester, which accelerates hydrogen atom transfer with the quinuclidine-derived radical cation through polarity-matching and/or ion-pairing effects.
REGIOSELECTIVE O-DEACYLATION OF FULLY ACYLATED GLYCOSIDES AND 1,2-O-ISOPORPYLIDENEALDOFURANOSE DERIVATIVES WITH HYDRAZINE HYDRATE
Ishido, Yoshiharu,Sakairi, Nobuo,Sekiya, Masao,Nakazaki, Nobuo
, p. 51 - 80 (2007/10/02)
On hydrazinolyis in 1:4 acetic acid-pyridine, and in pyridine, partisl O-deacylation of fully acylated methyl glycosides and some other glycosyl compounds ( 23 compounds ) was found to be induced, to give, in good yields, products bearing one free hydroxy