804566-03-8Relevant academic research and scientific papers
Nickel(II) chloride-mediated regioselective benzylation and benzoylation of diequatorial vicinal diols
Gangadharmath, Umesh B.,Demchenko, Alexei V.
, p. 2191 - 2193 (2004)
Ni(II)-chelates of monosaccharide vicinal diols were found to be useful intermediates in regioselective monobenzylation and monobenzoylation. It was observed that the substitution occurs exclusively at the position adjacent to the axially oriented substit
Selective mono-acylation of 1,2- and 1,3-diols using (α,α- difluoroalkyl)amines
Wakita, Natsumi,Hara, Shoji
experimental part, p. 7939 - 7945 (2010/10/19)
In the reaction of N,N-diethyl-α,α-difluorobenzylamine (DFBA) with 1,2- or 1,3-diols, selective mono-benzoylation occurs to afford mono-esters of the diols in good yield. The reaction is completed under mild conditions in a short reaction time. Further, prim-, sec-, and tert-diols and catechol can be converted to the corresponding mono-benzoates. DFBA is used for the protection of the hydroxy group in sugars. The selective mono-nicotinylation, formylation and pivaloylation of diols are also performed by using the corresponding difluoroalkylamines.
Acylation of carbohydrates over Al2O3: Preparation of partially and fully acylated carbohydrate derivatives and acetylated glycosyl chlorides
Tiwari, Pallavi,Misra, Anup Kumar
, p. 339 - 350 (2007/10/03)
Selective and per-O-acylation of carbohydrate derivatives using acyl chlorides and Al2O3, a solid support reagent, is reported. This protocol does not require the addition of any base or activator. This methodology has been further extended to the selective acylation of carbohydrate diols and the one-pot preparation of acetylated glycosyl chlorides direct from free reducing sugars. The yields obtained in most of the cases are excellent.
