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Nucleosides, Part LXIV , Base‐Labile Protecting Groups for the Oligoribonucleotide Synthesis
Author(s) -
Münch Ursula,
Pfleiderer Wolfgang
Publication year - 2001
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20010613)84:6<1504::aid-hlca1504>3.0.co;2-g
Subject(s) - chemistry , thymidine , reagent , protecting group , base (topology) , derivative (finance) , chloride , combinatorial chemistry , group (periodic table) , stereochemistry , organic chemistry , biochemistry , dna , mathematical analysis , alkyl , mathematics , financial economics , economics
New labile protecting groups for the anticipated synthesis of oligoribonucleotides were developed and introduced via their carbonochloridates 8 – 11 at the 5′ ‐O position of thymidine ( 15 ) to form 16 , 18 , 21 , and 24 in good yields ( Schemes 2 and 3 ). Similarly, the 5′‐ O ‐diphenylphosphinoyl(dpp)‐protected thymidine derivative 27 was synthesized with diphenylphosphinoyl chloride 14 as the reactive reagent. With the help of the model compounds 16 , 18 , 21 , 24 , and 27 , the deprotection rates of these functions towards base treatment were recorded to evaluate their usefulness as temporary protecting groups in RNA assembly ( Table ). Finally, the relative stability of the 2‐(4‐nitrophenyl)ethoxycarbonyl (npeoc) protecting group towards bases confirmed its use as a permanent blocking group in our npe/npeoc strategy.