7784-55-6

Usage

Chemical structure

A derivative of 2-deoxyglucose, a sugar closely related to glucose.

Acetylation

The compound is acetylated at four positions (1, 3, 4, and 6).

Functional group

Contains a 2,4-dinitrophenyl amino group.

Research applications

Often used as a derivative of 2-deoxyglucose in chemical and biochemical research.

Glucose metabolism

Utilized in studies related to glucose metabolism.

Glucose transport

Investigated in research on glucose transport and uptake in cells.

Insulin resistance and diabetes

Employed in studies related to insulin resistance and diabetes.

Identification and quantitation

Useful in identifying and quantifying glucose and glucose transporters in biological systems.
These properties and applications highlight the significance of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-[(2,4-dinitrophenyl)amino]hexopyranose in the field of biochemistry and its potential role in understanding and addressing glucose-related conditions.

Upstream product

• 70-34-8 2,4-Dinitrofluorobenzene 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 7253-54-5 2-deoxy-2-(2,4-dinitro-phenyl)amino-D-glucose 
• 108-24-7 acetic anhydride 
• 103637-78-1 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-α-D-glucopyranose hydrobromide 
• 58886-45-6 2-deoxy-2-(2,4-dinitroanilino)-D-glucose 

Downstream Products

• 3068-36-8 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitroanilino)-α-D-glucopyranosyl bromide 
• 84635-46-1 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-D-glucopyranose 
• 119324-38-8 benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-β-D-glucopyranoside 
• 104243-12-1 benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-α-D-glucopyranoside 
• 262599-58-6 benzyl O-(4-O-allyl-2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranoside 
• 262599-55-3 benzyl O-(4-O-acetyl-2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranoside 
• 262599-52-0 benzyl O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranoside 
• 262599-51-9 benzyl O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranoside 
• 262599-43-9 O-[3,4,6-tri-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranosyl]-(1->3)-1,2-di-O-benzyl-sn-glycerol 
• 262599-44-0 O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-1,2-di-O-benzyl-sn-glycerol 
• 262599-29-1 benzyl 3,4,6-tri-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranoside 
• 262599-28-0 benzyl 2-deoxy-2-(2,4-dinitroanilino)-6-O-trityl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Syntheses of N-aryl-protected glucosamines and their stereoselectivity in chemical glycosylations

N-Aryl-protecting groups were introduced in glucosamines to achieve β-selective glycosylation. Various N-aryl aminosugars were synthesized via Buchwald–Hartwig reaction. Glycosylation using glycosyl trichloroacetimidates of N-aryl aminosugars smoothly proceeded in the presence of trimethylsilyl trifluoromethanesulfonate. Use of a glycosyl donor comprising an electron-donating 2,4-dimethoxyphenyl (DMP) group led to the glycosylation proceeding with high β selectivity. This stereoselectivity seemed to be derived from the formation of an aziridine intermediate. The DMP-protecting group can be removed immediately by using ammonium hexanitratocerate (IV).