185754-26-1Relevant articles and documents
Rational Design of Mechanism-Based Inhibitors and Activity-Based Probes for the Identification of Retaining α-l-Arabinofuranosidases
Artola, Marta,Berrin, Jean-Guy,Davies, Gideon J.,Haon, Mireille,McGregor, Nicholas G. S.,Nin-Hill, Alba,Overkleeft, Herman S.,Ram, Arthur,Reijngoud, Jos,Rovira, Carme,Van Der Marel, Gijsbert A.,Van Wezel, Gilles P.,Codeé, Jeroen D. C.,Linzel, Dani?l,Rosso, Marie-No?lle
supporting information, p. 4648 - 4662 (2020/04/02)
Identifying and characterizing the enzymes responsible for an observed activity within a complex eukaryotic catabolic system remains one of the most significant challenges in the study of biomass-degrading systems. The debranching of both complex hemicell
Organocatalysis for the acid-free O-arylidenation of carbohydrates
Geng, Yiqun,Faidallah, Hassan M.,Albar, Hassan A.,Mhkalid, Ibrahim A.,Schmidt, Richard R.
supporting information, p. 7035 - 7040 (2013/11/06)
Methyl glycopyranosides of glucose, galactose, and mannose, their 2,3-di-O-benzyl-protected derivatives, as well as the unprotected sugars react with p-methoxybenzaldehyde dimethyl acetal (3) and with benzaldehyde dimethyl acetal (7) as reagents in the presence of thiourea 1 or squaramide 2 as the organocatalyst to afford regioselectively 4,6-O-arylidenated derivatives 5 and 8. With an excess amount of 3 or 7, diarylidenated derivatives are also obtained. In situ formation of acetals of type 3 and 7 from corresponding aldehydes 10 and 13 in the presence of an orthoester and organocatalyst 1 or 2 can be used to generate 5 and 8 directly from the aldehydes. Some substrates also lead to mixed orthoesters with this procedure. The reaction courses are discussed. A squaramide catalyzes the 4,6-O-arylidenation of glucose, mannose, and galactose with the use of arenecarbaldehyde dimethyl acetals or arenecarbaldehydes and orthoesters as the reagents. Glycoside derivatives also undergo this reaction. Copyright
Stripping off water at ambient temperature: Direct atom-efficient acetal formation between aldehydes and diols catalyzed by water-tolerant and recoverable vanadyl triflate
Chen, Chien-Tien,Weng, Shiue-Shien,Kao, Jun-Qi,Lin, Chun-Cheng,Jan, Mi-Dan
, p. 3343 - 3346 (2007/10/03)
(Chemical Equation Presented) Aromatic aldehydes can be readily protected as acetals with 1,2- and 1,3-diols by using vanadyl triflate as a catalyst in CH3CN at ambient temperature. Carbohydrate-based 1,2- and 1,3-diols can similarly be protected in good to excellent yields. The catalyst can be readily recovered from the aqueous layer. In combination with vanadyl triflate-catalyzed sequential regioselective, reductive acetal opening and chemoselective acylations, the title method allows for differential functionalization of all four hydroxyl units in a given glucopyranoside.