3254-14-6

Upstream product

• 57-88-5 cholesterol 
• 75172-83-7 3,4,6-Tri-O-acetyl-1,2-O-(1-<4-(4-biphenylyl)butyryloxy>ethyliden)-α-D-glucopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 88109-93-7 Z-12β-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-3α-hydroxydammar-20(22)-en-24-one 
• 19667-15-3 (3R,8R,10R,12R,14R)-17-[(R)-5-(1-Hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,12-diol 

Relevant academic research and scientific papers

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.

Research on Glucoside Synthesis, XI: Preparation and Properties of Acylorthoesters

Compounds with an acylorthoester structure 10a - e are prepared from 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide and silver salts of carboxylic acids in tetrahydrofuran.Compound 10e with a 4-(4-biphenylyl)butyryl residue proved to be relatively stab