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Synthesis of 5′-[(3-Aminooxypropyl)amino]-5′-deoxyadenosine

✍ Scribed by Kolb, Michael ;Barth, Jacqueline

Publisher
John Wiley and Sons
Year
1985
Tongue
English
Weight
295 KB
Volume
1985
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

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.

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