162426-12-2

Basic information

• Product Name: methyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-β-D-glucopyranoside
• Synonyms: methyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-β-D-glucopyranoside
• CAS NO: 162426-12-2
• Molecular Weight: 366.368
• Mol File: 162426-12-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-β-D-glucopyranoside(162426-12-2)
• EPA Substance Registry System: methyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-β-D-glucopyranoside(162426-12-2)

Safety Data

• Hazardous Substances Data: 162426-12-2(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 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 
• 709-50-2 methyl beta-D-glucopyranoside 
• 75-36-5 acetyl chloride 

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 articles and documents

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.

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.

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