251361-11-2Relevant academic research and scientific papers
Direct glycosylation of unprotected and unactivated sugars using bismuth nitrate pentahydrate
Polanki, Innaiah K.,Kurma, Siva H.,Bhattacharya, Asish K.
, p. 196 - 205 (2015/06/08)
Bi(NO3)3, a low-cost, mild, and environmentally green catalyst, has been successfully utilized for Fischer glycosylation for the synthesis of alkyl/aryl glycopyranosides by reacting unprotected sugars, namely, D-glucose, L-rhamnose, D-galactose, D-arabinose, and N-acetyl-D-glucosamine with various alcohols in good to excellent yields. The glycosides were formed with high α-selectivity. Further, an expedient separation of α- and β-glycosides using silver nitrate-impregnated silica gel flash liquid chromatography has been developed.
Synthesis and biological evaluation of coumarincarboxylic acids as inhibitors of gyrase B. L-rhamnose as an effective substitute for L-noviose
Ferroud, Didier,Collard, Jeannine,Klich, Michel,Dupuis-Hamelin, Claudine,Mauvais, Pascale,Lassaigne, Patrice,Bonnefoy, Alain,Musicki, Branislav
, p. 2881 - 2886 (2007/10/03)
A series of novobiocin-like coumarincarboxylic acids has been prepared bearing the L-rhamnosyl moiety as the sugar portion of the molecule. The similar DNA gyrase inhibitory activity of the novel class of coumarins to that of novobiocin demonstrates that L-rhamnose can effectively replace L-novoise. Introduction of alkyl side-chains at C-5 of coumarin leads to improved in vitro antibacterial properties in the novel series.
An improved synthesis of 4-O-benzoyl-2,2-difluorooleandrose from L- rhamnose. Factors determining the synthesis of 2,2-difluorocarbohydrates from 2-uloses
Barrena,Matheu,Castillon
, p. 2184 - 2188 (2007/10/03)
4-O-Benzoyl-2,2-difluorooleandrose (16) has been synthesized from L- rhamnose. The key steps are the formation of a difluoromethylene group in 12 by reacting ulose 11 with DAST and the chemoselective methylation of diol 13 to give compound 14. To obtain the 2,2-difluoro compound 12, the substituents in the neighborhood of the carbonyl group in ulose 11 must be equitorial and the sugar ring must have restricted conformational mobility. This was done using 1,1,2,2-tetramethoxycyclohexane (TMC) to protect the hydroxyls at positions 3 and 4 in the sugar ring.
