81058-28-8

Upstream product

• 81058-27-7 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide 
• 100-51-6 benzyl alcohol 
• 81058-26-6 1,2,3,4,6-penta-O-trimethylacetyl-β-D-glucopyranose 
• 3282-30-2 pivaloyl chloride 
• 162601-85-6 1,2-O-(1-N-Phenylethylideneamino-oxy)-2,2-dimethylpropylidene-3,4,6-tri-O-pivaloyl-α-D-glucopyranose 
• 14642-79-6 benzyloxy-trimethylsilane 
• 95898-06-9 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl fluoride 

Relevant academic research and scientific papers

Effective 1,2-trans-Glycosylation of Complex Alcohols and Phenols Using the Oximate Orthoester of O-Pivaloyl Glucopyranose

The highly stereoselective β-glycosylation of the complex steroid alcohols (2b)-(2d), the steroid phenol (2e), and the serine derivative (2f) is achieved in high yields using the new glycosyl donor 1,2-O-(1-N-1-phenylethylideneamino-oxy)-2,2-dimethylpropy

Stereoselective Glycosylation of Alcohols and Silyl Ethers Using Glycosyl Fluorides and Boron Trifluoride Etherate

The stereoselective glycosylation of alcohols and their silyl ethers has been achieved using O-alkyl-, O-acyl-, and acetal-protected glycosyl fluorides of the pyranose and furanose series and boron trifluoride etherate in CH2Cl2.

Glycoside Synthesis Using 2,3,4,6-Tetra-O-pivaloyl-α-D-glucopyranosyl Bromide

In the presence of silver salts the glycosylation of benzyl alcohol and of cholesterol is achieved in high yields by use of 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide (2).The formation of orthoesters, which often complicates the Koenigs-Knorr reaction using 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (5), is largely suppressed using 2.The preferential formation of the glycoside from the intermediate ion A is a result of the steric influence of the tert-butyl substituent which hinders nucleophilic attack at the acyloxonium carbon atom and steers the reaction in the desired direction.