Preparation of Pyrimidine Alkenyl Acyclic Nucleoside Phosphonoamidates | Zendy

Pileggi Elisa | Zendy; Serpi Michaela | Zendy; Pertusati Fabrizio | Zendy

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Preparation of Pyrimidine Alkenyl Acyclic Nucleoside Phosphonoamidates

Author(s) -

Pileggi Elisa,

Serpi Michaela,

Pertusati Fabrizio

Publication year - 2018

Publication title -

current protocols in nucleic acid chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.306

H-Index - 17

eISSN - 1934-9289

pISSN - 1934-9270

DOI - 10.1002/cpnc.56

Subject(s) - synthon , chemistry , pyrimidine , trimethylsilyl , nucleobase , aryl , alkylation , nucleoside , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , dna , biochemistry , alkyl

This synthetic protocol describes two strategies for the preparation of pyrimidine alkenyl acyclic nucleoside phosphonoamidates (ANPs), including linear and trisubstituted alkenyl derivatives. For the first procedure, a bis‐trimethylsilyl ester of the parent alkenyl ANPs is the key intermediate that reacts with the desired amino acid ester and aryl alcohol. For the second procedure, an allyl phosphonoamidate bearing the ProTide promoieties is the key synthon employed as olefin partner for a cross‐metathesis reaction with an alkylated nucleobase. © 2018 by John Wiley & Sons, Inc.

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