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Formation of anomeric phosphodiester linkages using H-phosphonate acceptors

✍ Scribed by Per J. Garegg; Jonas Hansson; Anne-Charlotte Helland; Stefan Oscarson

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
226 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new way of constructing anomeric glycosyl phosphodiester linkages has been explored.

Non-anomeric monosaccharide hydrogen phosphonate monoesters (5 and 9) have been used as acceptors in couplings using various benzylated galactosyl donors (trichloroacetimidate, thioglycoside, bromo and chloro sugars, 1-4, 7 and 8) and promoters to give, after oxidation, good yields of phosphodiester linked "disaccharides" (6 and 10), products usually obtained by using an anomeric hydrogen monophosphonate, a hydroxyl acceptor and pivaloyl chloride as coupling reagent.

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The Prooligonucleotide Approach: Synthesis of Mixed Phosphodiester and SATE Phosphotriester Prooligonucleotides Using H-Phosphonate and Phosphoramidite Chemistries
✍ Jean-Charles Bologna; FranΓ§ois Morvan; Jean-Louis Imbach πŸ“‚ Article πŸ“… 1999 πŸ› John Wiley and Sons 🌐 English βš– 232 KB πŸ‘ 1 views

The synthesis of mixed SATE-phosphotriester and phospho-linkages to yield thiono-or oxo-triester SATE and thiono-or oxo-diester linkages. This approach allows the synthesis of diester prooligonucleotides using both phosphoramidite and H-phosphonate chemistries is described. The key step is the any d