A MILD AND RAPID GLYCOSYLATION REACTION BETWEEN PYRIMIDINE-BASES AND 2-DEOXYRIBOFURANOSYL N,N,N',N'-TETRAMETHYLPHOSPHOROAMIDATES

Authors
IIMORI T KOBAYASHI H HASHIMOTO S IKEGAMI S
Citation
T. Iimori et al., A MILD AND RAPID GLYCOSYLATION REACTION BETWEEN PYRIMIDINE-BASES AND 2-DEOXYRIBOFURANOSYL N,N,N',N'-TETRAMETHYLPHOSPHOROAMIDATES, Heterocycles, 42(2), 1996, pp. 485-488
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
42
Issue
2
Year of publication
1996
Pages
485 - 488
Database
ISI
SICI code
0385-5414(1996)42:2<485:AMARGR>2.0.ZU;2-9
Abstract
A trimethylsilyl triflate-mediated coupling reaction to produce protec ted 2'-deoxynucleosides has been developed by using N,N,N',N'-tetramet hyl-phosphoroamidate as a leaving group. In this reaction, employment of a 3,4,5-trimethoxybenzoyl group as the 3-hydroxyl protective group in the sugar moiety improved the beta-stereoselectivity via a novel Id -participation.