Solvent-Free Synthesis of DecylD-Glycopyranosides Under Focused Microwave Irradiation

Efficient Acetylation of Carbohydrates Promoted by Imidazole

“…[4,5] Besides some classical reaction protocols for the acetylation of carbohydrates, [6][7][8] a variety of reagents have been developed for the acetylation of carbohydrate derivatives avoiding the use of pyridine which includes several Lewis acid catalysts [9][10][11][12][13][14] and a number of heterogeneous catalysts. [15][16][17][18] ZnCl 2 /sodium acetate combination [19] or InCl 3 [20] with acetic anhydride under microwave conditions have also been reported recently for the acetylation of carbohydrates. Few reports have also appeared on the acetylation of carbohydrates using ionic liquids as solvents and catalysts.…”

Microwave-assisted synthesis of long-chain alkyl glucopyranosides

“…11 We show that this methodology can be applied to the glucosylation of several alcohols from hexanol to hexadecanol (Scheme 1). Variation in yield and anomeric composition depends on the irradiation time and on the length of the carbon chain of the alcohol.…”

“…Fischer glycosylation of fatty alcohols has been employed despite the low solubility of glucose in long-chain fatty alcohols. [7][8][9][10][11] By this methodology, it is usual to obtain a mixture of four isomers: the kinetic furanosides and the thermodynamic pyranosides with the major axial anomeric configuration. A protected glucose is used in the Koenigs-Knorr [12][13][14][15] and the Helferich [15][16][17][18][19][20][21][22] glycosylations of fatty alcohols.…”

Acylation of carbohydrates over Al2O3: preparation of partially and fully acylated carbohydrate derivatives and acetylated glycosyl chlorides

“…9,10 Sometimes, pyridine derivatives such as 4-(N,N-dimethylamino)pyridine and 4-(pyrrolidino)pyridine are added as a cocatalyst to speed up the acylation. 11,12 A variety of other catalysts in combination with excess acetic anhydride and solvent have been employed in the acetylation of carbohydrate derivatives, including sodium acetate, 13 sulfuric acid, 14 perchloric acid, 15 and a number of Lewis acid catalysts such as, iodine, 16 Sc(OTf) 3 , 17 Cu(OTf) 2 , 18 CoCl 2 , 19 ZnCl 2 , 20 BiOCl-SOCl 2 , 21 LiClO 4 , 22 FeCl 3 , 23 BiCl 3 , 24 and a series of heterogeneous catalysts such as, montmorillonite K-10, 25 zeolites, 26 nafion-H. 27 Recently, a ZnCl 2 -sodium acetate combination 28 or InCl 3 29 with acetic anhydride under microwave condition has been reported for the acetylation of carbohydrates. A few reports have also appeared on the acetylation of carbohydrates using ionic liquids as solvents and catalysts.…”