20771-12-4

Upstream product

• 88037-29-0 methyl 4-O-acetyl-6-O-trityl-β-D-glucopyranoside 
• 108-05-4 vinyl acetate 
• 709-50-2 methyl beta-D-glucopyranoside 
• 141-78-6 ethyl acetate 
• 4860-85-9 methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 2466-76-4 N-Acetylimidazole 
• 6988-40-5 methyl 2,3-di-O-benzyl-β-D-glucopyranoside 
• 51842-15-0 methyl 2,3-di-O-benzyl-4-O-acetyl-6-O-trityl-β-D-glucopyranoside 
• 51842-38-7 methyl 2,3-di-O-benzyl-6-O-trityl-β-D-glucopyranoside 
• 153874-61-4 methyl 6-O-<2-(methoxycarbonyl)acetyl>-β-D-glucopyranoside 
• 75-36-5 acetyl chloride 
• 79384-28-4 methyl 6-O-(2-carboxyacetyl)-β-D-glucopyranoside 

Relevant academic research and scientific papers

Selective Acetylation of the Primary Hydroxyl Group in Methyl D-Hexopyranosides with a Mixture of Acetic Anhydride and Acetic Acid

Abstract—: 6-O-Acetylated derivatives of D-hexopyranosides are valuable intermediates in synthetic carbohydrate chemistry. We have developed a new simple procedure for selective acetylation of the primary hydroxyl group in methyl D-hexopyranosides consisting in treatment with a mixture of acetic anhydride and acetic acid at 50°C. As a result, corresponding 6-acetates were formed in 40–50% yield.

A basic germanodecatungstate with a - 7 charge: Efficient chemoselective acylation of primary alcohols

The synthesis of highly negatively charged polyoxometalates with electrically and structurally controlled uniform basic sites can lead to the unique base catalysis. In this work, a γ-Keggin germanodecatungstate, [γ-HGeW10O36]7- (A), having a -7 charge was, for the first time, successfully synthesized by the reaction of [γ-H2GeW10O36]6- with one equivalent of [(n-C4H9)4N]OH under non-aqueous conditions. The activities of germanodecatungstates for base-catalyzed reactions dramatically increased with increase in the number negative charges from -6 to -7. In the presence of A, various combinations of acylating agents and primary alcohols including those with acid-sensitive functional groups chemoselectively gave the desired acylated products in high yields even under the stoichiometric conditions.

Regioselective acetylation of carbohydrates and diols catalyzed by tetramethyl-ammonium hydroxide in water

A novel method for an efficient regioselective acetylation of carbohydrates and diols in aqueous solution is described. Treatment of substrates with 1-acetylimidazole, and tetramethyl-ammonium hydroxide (TMAH) in water under mild conditions gave highly regioselective acetylation for primary hydroxyl groups. This discovery provides an eco-friendly way for selective acetylation of non-protected glycosides and diols in water, avoiding the use of toxic organic solvents and the necessity of pre-protection of secondary hydroxyl groups. This journal is

A dramatic effect of the ionic liquid structure in esterification reactions in protic ionic media

Bronsted acidic ionic liquids (ILs) have been synthesized and investigated as catalysts in esterification and transesterification reactions: simple and non-corrosive salts characterized by aliphatic cations associated with an "acidic" anion (in particular, [HSO4]-) gave the higher yields. A quite good correlation between IL acidity (H 0) and catalytic ability was found although also the hydrophilic nature of the ionic medium probably affects the process efficiency.

Carbohydrate esterases of family 2 are 6-O-deacetylases

Three acetyl esterases (AcEs) from the saprophytic bacteria Cellvibrio japonicus and Clostridium thermocellum, members of the carbohydrate esterase (CE) family 2, were tested for their activity against a series of model substrates including partially acet

Reagent-dependent regioselective control in multiple carbohydrate esterifications

(Chemical Equation Presented) Regioselective control in organotin-mediated multiple acylation of carbohydrates is presented. The acylation reagent could be efficiently used to direct the product formation. Reagent-dependent thermodynamic and kinetic contr

Mode of action on deacetylation of acetylated methyl glycoside by cellulose acetate esterase from Neisseria sicca SB

The regioselective deacetylation of purified cellulose acetate esterase from Neisseria sicca SB was investigated on methyl 2,3,4,6-tetra-O-acetyl- β-D-glucopyranoside and 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside. The substrates were used as model comp

METHANOLYSIS OF ACETYLATED SUGARS AND GLYCOSIDES IN THE PRESENCE OF TIN OXIDES AND ALKOXIDES

A simple, regioselective O-deacetylation procedure is described which involves > OH > OMe.No acyl migration took place under the reaction conditions.

A reversal in the order of H-6R and H-6S chemical shifts of some aldohexopyranose derivatives, associated with the acetylation of OH-4 and OH-6 groups. A distinction between 3- and 4-linked D-glucose residues in disaccharides

On peracetylation of methyl α- or β-D-glucopyranose, there is a reversal in the order of the chemical shifts of the 6,6'-methylene protons, i.e., whereas the H-6S signal appears downfield of H-6R in the spectra of the glucosides, the