Reliable method for the synthesis of aryl β-D-glucopyranosides, using boron trifluoride–diethyl ether as catalyst

Abstract

Reliable method for the synthesis of aryl β-D-glucopyranosides, using boron trifluoride-diethyl ether as catalyst Smits, Elly; Engberts, Jan; Kellogg, Richard M.; Doren, Henk A. van Take-down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim.Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons the number of authors shown on this cover page is limited to 10 maximum. Stereospecific formation of aryl 2,3,4,6-tetra-O-acetyl-β β-D-glucopyranosides was achieved by reaction of penta-O-acetyl-β β-D-glucose 1 with substituted phenols in the presence of boron trifluoride. Yields of the purified products varied from 52-85%. Benzyl alcohol could also be glucosylated using similar conditions. All products were purified by crystallization from ethanol. The purity and the anomeric configuration of the products were determined by means of 1 H and 13 C NMR spectroscopy, melting points and optical rotation.

Glycosidation–Anomerisation Reactions of 6,1‐Anhydroglucopyranuronic Acid and Anomerisation of β‐D‐Glucopyranosiduronic Acids Promoted by SnCl4

“…Such studies would also indicate whether the anomerisation reactions of glucuronic acids and related compounds would have potential in preparative chemistry. In addition to 3, [10] 11 d [11] and 11 e, [12] the glucopyranosides 17 a, [13] 17 b [14] and 17 c, [15] and the esters of glucopyranosiduronic acid 18 b [16] and 19 a [10] were obtained by literature procedures. The allyl esters 19 b and 19 c were synthesised from the trichloroacetimidate donor 22 (Scheme 3).…”

Aromatic O-glycosylation

“…SnCl 4 , p-toluenesulfonic acid (pTSA) and other Lewis acids have also been used, but most often with substantially lower yields. 27,28 The yields and reaction rates are clearly dependent on the nucleophilicity of the phenol; electron donating groups (e.g., alkoxy) usually give better yields. Generally, substituents in the ortho-position tend to give lower yields irrespective of the electronic properties (Scheme 4).…”

Synthesis of d-glucose and l-phenylalanine substituted phenylene–thiophene oligomers

“…The value is typical of the axial-axial arrangement in the b anomer. 21 The reaction of 16 with NaOH, followed by addition of 6-bromohexanol, afforded the derivative 18. The esterification reaction of the alcohol 18 with the BOC-N-protected L-phenylalanine was performed using isopropenyl chlorocarbonate (IPCC) as the condensing agent, according to our previously reported procedure.…”