705254-57-5

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 705254-56-4 9-[3-hydroxy-2-(hydroxymethyl)prop-1-enyl]-N-2-isobutyrylguanine 
• 663193-28-0 9-[3-benzyloxy-2-(benzyloxymethyl)-2-(diethoxythiophosphoryloxy)propyl]-N-2-isobutyrylguanine 
• 663193-25-7 2-amino-9-[3-benzyloxy-2-(benzyloxymethyl)-2-hydroxypropyl]-N-2-isobutyrylguanine 
• 705254-55-3 9-[3-benzyloxy-2-(benzyloxymethyl)prop-1-enyl]-N-2-isobutyrylguanine 
• 663193-21-3 2-amino-9-[3-benzyloxy-2-(benzyloxymethyl)-2-hydroxypropyl]guanine 
• 663193-17-7 2-amino-9-[3-benzyloxy-2-(benzyloxymethyl)-2-hydroxypropyl]-6-chloropurine 
• 10310-21-1 2-Amino-6-chloropurin 

Relevant academic research and scientific papers

Improved synthesis of oligonucleotides with an allylic backbone. Oligonucleotides containing acyclic, achiral nucleoside analogues: N-1 or N-9-[3-hydroxy-2-(hydroxymethyl)prop-1-enyl]nucleobases

An improved phosphoramidite method is described to prepare oligonucleotides modified with the acyclic, achiral monomers 1. Examination of dimers, prepared on solid support or in solution, showed that phosphortriester dimers containing the allylic unit 1 were unstable towards bases, whereas phosphordiester dimers were stable. Phosphordiester dimers were obtained by replacing cyanoethyl phosphoramidites 2 with phosphoramidites 3, which gave phosphordiesters directly upon oxidation. The phosphordiester dimers were found to be stable towards capping and oxidation, but were somewhat labile towards acids. By reducing the contact time to acids during detritylation it was possible to prepare oligonucleotides containing 4 or 8 modified A, G or T units. The modified oligonucleotides hybridized to complementary DNA and RNA, although with reduced affinity (ΔTm per modification -1 to -5°C). The Royal Society of Chemistry 2006.

Preparation and antiviral properties of new acyclic, achiral nucleoside analogues: 1- or 9-[3-hydroxy-2-(hydroxymethyl)prop-1-enyl]nucleobases and 1- or 9-[2,3-dihydroxy-2-(hydroxymethyl)propyl]nucleobases.

Acyclic, achiral nucleoside derivatives 1b-e of adenine, cytosine, 5-methylcytosine, and guanine, containing a 3-hydroxy-2-(hydroxymethyl)prop-1-enyl group on N-1 or N-9, have been prepared analogously to the previously described thymine derivative 1a. In contrast to the adenine and guanine derivatives, the cytosine derivative 9 was unstable, and was obtained in a low yield due to side reactions. These include cleavage of the propenyl group from the base, and the formation of a bicyclic compound. The thymine derivative, although stable under neutral conditions, likewise underwent a reversible cyclization reaction (Michael addition) in the presence of acids or bases. The 5-methylcytosine derivative was stable under neutral and basic conditions. Four other nucleoside derivatives 26a-d containing a 2,3-dihydroxy-2-(hydroxymethyl)propyl group on N-1 or N-9, three of which are new, have likewise been prepared. All compounds were evaluated as antiviral agents against HIV-1 and HSV-1 but were devoid of antiviral activity.