143056-35-3

Basic information

• Product Name: N²-Acetyl-2-amino-6-chloro-9-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)purine
• CAS NO: 143056-35-3
• Molecular Weight: 790.186
• Mol File: 143056-35-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N²-Acetyl-2-amino-6-chloro-9-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)purine(CAS DataBase Reference)
• NIST Chemistry Reference: N²-Acetyl-2-amino-6-chloro-9-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)purine(143056-35-3)
• EPA Substance Registry System: N²-Acetyl-2-amino-6-chloro-9-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)purine(143056-35-3)

Safety Data

• Hazardous Substances Data: 143056-35-3(Hazardous Substances Data)

Upstream product

• 10310-21-1 2-Amino-6-chloropurin 
• 7602-01-9 N-(6-chloro-7⁽⁹⁾H-purin-2-yl)-acetamide 
• 112841-30-2 1-O-acetyl-2,3,4,6-tetra-O-benzoyl-α-D-glucopyranose 

Relevant articles and documents

Synthesis of 2-aminopurine nucleosides via regiocontrolled glycosylation

The stereo- and regiocontrolled synthesis of pyranosyl 2-aminopurine nucleosides is described. Coupling of bissilylated N2-acetyl-2-aminopurine with peracetylated glucopyranosides (SnCl4, (CH2Cl)2-MeCN, reflux) afforded good yields of the corresponding N9-β-2-aminopurine nucleosides. Glycosylation of N2-acetyl-2-amino-6-chloropurine could be made to produce either N9-nucleosides (TMSOTf, (CH2Cl)2, reflux), or N7-nucleosides (SnCl4/MeCN, room temperature) selectively. Application of Knapp's thioglycoside procedure (NIS + TfOH, (CH2Cl)2, room temperature) produced the N9-nucleosides with either base. The 2-amino-6-chloropurine derivatives were converted to their corresponding 2-aminopurine nucleosides by hydrogenolysis (H2, Pd/C). A convenient NOESY protocol for establishing base regiochemistry and anomeric stereochemistry is also presented.