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Synthesis of 3′‐Alkylthio‐2′,3′‐dideoxy Nucleosides with Potential Anti‐HIV Activity from 2‐Deoxy‐D‐ribose, Using a Phosphorus Pentoxide Reagent
Author(s) -
Dueholm Kim L.,
Motawia Mohammed S.,
Pedersen Erik B.,
Nielsen Claus,
Lundt Inge
Publication year - 1992
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19923250914
Subject(s) - chemistry , anomer , thymine , acetic anhydride , silylation , pyridine , uracil , reagent , nucleobase , cytosine , ribose , acetylation , organic chemistry , hydrazide , chloroform , guanine , stereochemistry , nucleotide , catalysis , dna , biochemistry , gene , enzyme
Direct condensation of 2‐deoxy‐D‐ribose ( 1 ) with mercaptans using the P 4 O 10 /H 2 O/Bu 3 N reagent in chloroform resulted in coupling at C‐3 to give the anomeric mixtures of the corresponding pentopyranoses 2 and pentofuranoses 3 , After acetylation with acetic anhydride in dry pyridine of these 3‐alkylthio pentofuranoses, coupling with the nucleobases uracil, thymine, and cytosine in accordance with the Friedel ‐ Crafts catalyzed silyl Hilbert ‐ Johnson method yielded the acetylated D‐ erythro nucleosides 7 as anomeric mixtures, separable only by means of chromatography either before or after deprotection with ammonia. The nucleosides 8a‐e were devoid of any activity against HSV‐1 and HIV‐1.