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Synthesis and Structural Elucidation of 2′‐Deoxy‐4′‐thio‐ L ‐ threo ‐pentofuranosylpyrimidine and ‐purine Nucleosides
Author(s) -
Wirsching Jörn,
Voss Jürgen,
Adiwidjaja Gunadi,
Giesler Anja,
Kopf Jürgen
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200103)2001:6<1077::aid-ejoc1077>3.0.co;2-0
Subject(s) - chemistry , thio , stereochemistry , cytidine , purine , nucleoside , derivative (finance) , hypoxanthine , purine nucleoside phosphorylase , anomer , organic chemistry , enzyme , financial economics , economics
Benzyl 3,5‐di‐ O ‐benzyl‐2‐deoxy‐1,4‐dithio‐ L ‐ threo ‐pentofuranoside ( 13 ) was used as glycosyl donor for the synthesis of 4′‐thio‐ L ‐ threo ‐pentofuranosyluracil derivatives 23−29 . The corresponding cytidine analogue 33 was prepared from 13 via the triazolo derivative 31 . Adenine and hypoxanthine did not react with 13 . Therefore, 13 was transformed into the 1‐ O ‐acetate 15 , which was a sufficiently reactive donor for the purine bases, yielding 4′‐thio‐ L ‐ threo ‐pentofuranosylpurines 36 and 37 . In most cases it was possible to obtain pure anomers of the deprotected nucleoside analogues, three of which were suitable for X‐ray structural analyses.