143056-36-4Relevant articles and documents
Synthesis of 2-aminopurine nucleosides via regiocontrolled glycosylation
Garner, Philip,Yoo, Ji Uk,Sarabu, Ramakanth
, p. 4259 - 4270 (2007/10/02)
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.