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Synthesis of 5′‐[(3‐Aminooxypropyl)amino]‐5′‐deoxyadenosine
Author(s) -
Kolb Michael,
Barth Jacqueline
Publication year - 1985
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198519850517
Subject(s) - chemistry , deoxyadenosine , alkylation , derivative (finance) , yield (engineering) , derivatization , adenosine , medicinal chemistry , salt (chemistry) , benzene , stereochemistry , organic chemistry , high performance liquid chromatography , biochemistry , catalysis , financial economics , economics , metallurgy , materials science
The synthesis of the title compound 2 is described. N ‐Alkylation of 5′‐amino‐5′‐deoxy‐2′,3′‐ O ‐(1‐methylethylidene)adenosine ( 3 ) with [(3‐iodopropoxy)methyl]benzene gave after debenzylation the 5′‐deoxyadenosine derivative 4b . After derivatization of the 5′‐NH, the terminal hydroxy group was reacted with triphenylphosphane, diethyl azodicarboxylate, and N ‐hydroxyphthalimide to yield a full protected derivative of 2 . Sequential deprotection (H 2 NNH 2 , then H 2 SO 4 ) afforded the target molecule 2 as its sesquisulfate salt.