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Synthesis of New 3′‐Deoxyribonucleosides Employing the Acid‐Catalyzed Fusion Method
Author(s) -
Volpini Rosaria,
Camaioni Emidio,
Costanzi Stefano,
Vittori Sauro,
Cristalli Gloria
Publication year - 1998
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/(sici)1522-2675(19981216)81:12<2326::aid-hlca2326>3.0.co;2-4
Subject(s) - chemistry , anomer , synthon , epimer , glycosylation , pyridine , catalysis , regioselectivity , derivative (finance) , stereochemistry , glycal , uracil , deoxyribonucleosides , organic chemistry , stereoselectivity , biochemistry , financial economics , economics , enzyme , dna
Coupling of 4,6‐dichloro‐1 H ‐imidazo[4,5‐ c ]pyridine (2,6‐dichloro‐3‐deaza‐9 H ‐purine) ( 1 ) with 1,2‐ O ‐di‐acetyl‐5‐ O ‐benzoyl‐3‐deoxy‐ β ‐ D ‐ribofuranose ( 2 ), employing the acid‐catalyzed fusion method, is reported ( Scheme 1 ). The condensation reaction was regioselective and gave the three N 1 ‐glycosylation products 3 – 5 , whereas no N 3 ‐nucleosides were detected. Treatment of 3 – 5 with methanolic ammonia afforded the corresponding deprotected nucleosides 6 – 8 . Compounds 6 and 7 were assigned the structure of the β ‐ D ‐ and α ‐ D ‐anomeric N 1 ‐(3′‐deoxyribo)nucleosides, respectively. The third derivative 8 proved to be the α ‐ D ‐anomer of a 3′‐deoxyarabinonucleoside deriving from epimerization at C(2) of the sugar. The 2‐chloro‐ and N 6 ‐substituted derivatives 9 , 11 , and 13 of 3′‐deoxy‐3‐deazaadenosine ( 10 ) and of its α ‐ D ‐anomer 12 can be obtained from these versatile synthons ( Schemes 2 and 3 ).