81058-29-9

Basic information

• Product Name: 1,2-O-(1-Benzyloxyneopentyliden)-3,4,6-tri-O-pivaloyl-α-D-glucopyranose
• CAS NO: 81058-29-9
• Molecular Weight: 606.754
• Mol File: 81058-29-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,2-O-(1-Benzyloxyneopentyliden)-3,4,6-tri-O-pivaloyl-α-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-O-(1-Benzyloxyneopentyliden)-3,4,6-tri-O-pivaloyl-α-D-glucopyranose(81058-29-9)
• EPA Substance Registry System: 1,2-O-(1-Benzyloxyneopentyliden)-3,4,6-tri-O-pivaloyl-α-D-glucopyranose(81058-29-9)

Safety Data

• Hazardous Substances Data: 81058-29-9(Hazardous Substances Data)

Upstream product

• 81058-26-6 1,2,3,4,6-penta-O-trimethylacetyl-β-D-glucopyranose 
• 3282-30-2 pivaloyl chloride 
• 81058-27-7 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide 
• 100-51-6 benzyl alcohol 

Relevant articles and documents

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.