162426-12-2

Upstream product

• 75-36-5 acetyl chloride 
• 71117-37-8 (2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 108-24-7 acetic anhydride 
• 709-50-2 methyl beta-D-glucopyranoside 

Downstream Products

• 162284-49-3 methyl 2,3-di-O-acetyl-6-O-benzyl-β-D-glucopyranoside 
• 556814-87-0 methyl 4-O-(2,3,4,6-tetrakis-O-(p-bromobenzoyl)-β-D-glucopyranosyl)-2,3-di-O-acetyl-6-O-benzyl-β-D-glucopyranoside 
• 556814-91-6 methyl 4-O-(2,3,4,6-tetrakis-O-(p-bromobenzoyl)-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-α-D-glucopyranoside 
• 556814-89-2 methyl 4-O-(2,3,4,6-tetrakis-O-(p-bromobenzoyl)-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 
• 556814-88-1 methyl 2,3-di-O-acetyl-4-O-[2,3,4,6-tetrakis-O-(4-bromobenzoyl)-β-D-glucopyranosyl]-β-D-glucopyranoside 

Relevant academic research and scientific papers

Efficient one-pot per-: O -acetylation-thioglycosidation of native sugars, 4,6- O -arylidenation and one-pot 4,6- O -benzylidenation-acetylation of S -/ O -glycosides catalyzed by Mg(OTf)2

A sequential one-pot per-O-acetylation-S-/O-glycosidation of native mono and disaccharides under solvent free conditions using 0.5 mole% of Mg(OTf)2 as a non-hygroscopic, recyclable catalyst is reported. Regioselective 4,6-O-arylidenation of glycosides and thioglycosides with benzaldehyde or p-methoxybenzaldehyde dimethyl acetal is catalyzed by 10 mole% of Mg(OTf)2 to produce the corresponding 4,6-O-arylidenated product in high yields. Mg(OTf)2 can also mediate sequential one-pot benzylidenation-acetylation of mono and disaccharide based glycosides and thioglycosides in high yield.

Sulfuric acid immobilized on silica: an efficient promoter for one-pot acetalation-acetylation of sugar derivatives

Sulfuric acid immobilized on silica gel has been used as an efficient and safe alternative promoter for acetalation and subsequent acetylation of sugar glycosides using stoichiometric reagents without work-up. The synthesis of different types of per-O-ace

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

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.

Efficient acetylation of carbohydrates promoted by imidazole

An efficient per-O-acetylation of carbohydrate derivatives and unprotected reducing sugars promoted by imidazole is reported. The reaction conditions have been successfully employed to acetylate carbohydrate derivatives containing acid-susceptible functional groups. In most of the cases the yields obtained were excellent. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

Hydroxymethyl rotamer populations in disaccharides

Sixteen methyl glucopyranosyl glucopyranoside disaccharides (methyl β-D-Glcp(p-Br-Bz)-(1→x)-β/ α-D-Glcp) containing β-glycosidic linkages (1→2, 1→3, 1→4, and 1→6) were synthesized and analyzed by means of CD and NMR spectroscopy in three different solvent