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Dealkylation of nucleoside arylmethyl 2-chlorophenyl phosphates: the 2,4-dinitrobenzyl protecting group

✍ Scribed by Chris Christadoulou; Colin B. Reese

Book ID
104217045
Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
274 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

Following a study of the effect of benzyl substitution on the rates of nucleophilic dealkylation of phosphotriesters, 2,4-dinitrobenzyl is proposed as a temporary protecting group for 3'-terminal phosphodiester functions in oligonucleotide synthesis.

Kinetic data indicate1 that the effect of nuclear substitution on the rates of displacement reactions of benzyl halides is complex. Many years ago, Bennett and Jones showed2 that,

πŸ“œ SIMILAR VOLUMES

Use of the 2,4-dinitrobenzyl protecting
Use of the 2,4-dinitrobenzyl protecting group in the synthesis of phosphorodithioate analogues of oligodeoxyribonucleotides
✍ Geoffrey M. Porritt; Colin B. Reese πŸ“‚ Article πŸ“… 1990 πŸ› Elsevier Science 🌐 French βš– 267 KB

Susnnary: The putative intermediate bis(l,2,4-triazolide) derivative (I) is used in the stepwise synthesis in solution of the phosphorodithioate analogue (l0) of thymiaylyl-(3'+5')-thymidylyl-(3'+5')-thymidine; the 2,4-dinitrobensyl (Dnb) group is used to protect phosphorodithioate internucleotide l