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Free‐radical synthesis of 3‐(2‐cyanoethyl)‐ and 3‐(2‐methoxycarbonylethyl)‐2,3‐dideoxy‐α‐D‐ Erythro ‐pentofuranoside and their application in the synthesis of potential antiviral nucleosides
Author(s) -
Lau Jesper,
Walczak Krzysztof,
Pupek Krzysztof,
Buch Carsten,
Nielsen Carsten M.,
Pedersen Erik B.
Publication year - 1991
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.2503241203
Subject(s) - chemistry , tributyltin hydride , acrylonitrile , anomer , free radical reaction , purine nucleoside phosphorylase , methyl acrylate , nucleoside , diastereomer , stereochemistry , coupling reaction , organic chemistry , radical , purine , copolymer , catalysis , enzyme , polymer
Abstract Free‐radical reaction of different carbohydrate educts 2, 5, and 7 with acrylonitrile in the presence of tributyltin hydride and a radical initiator (AIBN) gave the methyl 3‐(2‐cyanoethyl)‐2,3‐dideoxypentofuranosides 3a and 6. Similar reaction of 2 with methyl acrylate gave 3‐(2‐methoxycarbonylethyl>‐2,3‐dideoxypentofuranose 3b. Nucleoside coupling of 3a with silylated uracil gave an anomeric mixture of β‐ and α‐nucleoside 8 and 9 which were deprotected to give 10 and 11, respectively. Similar reaction of 3b with silylated N 4 ‐isobutyrylcytosine gave 12 and 13 which were deprotected to give the final nucleosides 16 and 17, respectively. None of the compounds 10a, 11, 14‐17 showed significant activity against HIV.