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Synthesis of 6‐dimethylaminopurine 2′,3′‐dideoxynucleosides
Author(s) -
Motawia Mohammed S.,
ElTorgoman Abdel Moneim,
Pedersen Erik B.
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1991199101152
Subject(s) - chemistry , yield (engineering) , deoxyribose , trimethylsilyl , anomer , trifluoromethanesulfonate , stereochemistry , medicinal chemistry , catalysis , nucleic acid , organic chemistry , biochemistry , materials science , metallurgy
The trimethylsilyated 6‐dimethylaminopurine 1 was coupled with the 2′,3′‐dideoxyribose derivatives 2a, b and 7 by using trimethylsilyl triflate as catalyst to yield the corresponding nucleosides 3a, b, 4a, b and 8 , which were appropriately deprotected to give the desired nucleosides 5a, b and 9 as well as the related α‐isomers 6a, b and 10 . The 2‐deoxyribose derivative 12 was mesylated at the 3′‐ O ‐position to give 13 which was coupled similarly with 1 to yield compound 14 and its α‐anomer 15 . Compounds 14 and 15 were treated with tetrabutylammonium fluoride to give the desired 2′,3′‐didehydro‐2′,3′‐dideoxynucleoside analogue 16 and its α‐anomer 17 .