14687-09-3

Basic information

• Product Name: 2,3,4,6-tetra-O-acetyl-1-O-(p-nitrobenzoyl)-β-D-glucopyranose
• CAS NO: 14687-09-3
• Molecular Weight: 497.413
• Mol File: 14687-09-3.mol

Chemical Properties

• CAS DataBase Reference: 2,3,4,6-tetra-O-acetyl-1-O-(p-nitrobenzoyl)-β-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-tetra-O-acetyl-1-O-(p-nitrobenzoyl)-β-D-glucopyranose(14687-09-3)
• EPA Substance Registry System: 2,3,4,6-tetra-O-acetyl-1-O-(p-nitrobenzoyl)-β-D-glucopyranose(14687-09-3)

Safety Data

• Hazardous Substances Data: 14687-09-3(Hazardous Substances Data)

Upstream product

• 75474-03-2 p-nitrobenzoic acetic anhydride 
• 81342-44-1 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 3947-62-4 2,3,4,6-tetraacetylglucose 
• 78942-86-6 2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-α-D-glucopyranose 
• 62-23-7 4-nitro-benzoic acid 

Relevant articles and documents

Studies of Carbohydrates IV. A Novel Highly Stereoselective Synthesis of 1-O-Acyl-β-D-glucopyranose Tetraacetates via the Glucosyl Trifluoroacetate

2,3,4,6-Tetra-acetyl-glucose (1) reacted with trifluoroacetic anhydride to give good yield of 2,3,4,6-tetra-O-acetyl-1-α-O-trifluoroacetyl-α-D-glucopyranose (2) wich was converted into corresponding 1-O-acyl-β-D-glucopyranose tetraacetates. β-Anomers of g

2-(Trimethylsilyl)ethyl Glycosides. Synthesis, Anomeric Deblocking, and Transformation into 1,2-Trans 1-O-Acyl Sugars

Twenty-seven mono --> tetrasaccharidic 2-(trimethylsilyl)ethyl (TMSET) glycosides were synthesized by the Koenigs-Knorr-type method in combination with a wide range of standard reagents for glycoside synthesis and protecting-group chemistry.Variously protected TMSET glycosides were treated with BF3*Et2O (0.7-0.8 equiv) and different carboxylic anhydrides (1.1-15 equiv) in toluene at 22-55 deg C, which gave in one step the corresponding protected 1-O-acyl sugars.In the majority of cases, the yields of purified compounds exceeded 90percent and the anomeric configuration of the starting TMSET glyoside was conserved to a large extent (>95percent) in most of the 1-O-acylated products.Unprotected and acetyl-, benzoyl-, benzyl-, dimethyl-tert-butylsilyl-, and phthaloyl-protected mono-->tetrasaccharidic TMSET glycosides were anomerically deblocked by using trifluoroacetic acid in dichloromethane at 0-22 deg C for 10-30 min.The hemiacetal products were isolated in 88-96percent yield; all reagents and byproducts were volatile and easily removed.