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Mitsunobu Alkylation of Cancerostatic 5‐Fluorouridine with (2 E )‐10‐Hydroxydec‐2‐enoic Acid, a Fatty Acid from Royal Jelly with Multiple Biological Activities
Author(s) -
Ottenhaus Vanessa,
Rosemeyer Helmut
Publication year - 2015
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201500048
Subject(s) - chemistry , residue (chemistry) , mitsunobu reaction , alkylation , nucleoside analogue , nucleoside , fatty acid , organic chemistry , stereochemistry , catalysis
Abstract 5‐Fluorouridine ( 1 ) – a nucleoside antimetabolite with strong cancerostatic properties – was protected i ) at the 2′‐ and 3′‐OH groups with a heptan‐4‐ylidene residue and ii ) at the 5′‐OH group with a (4‐methoxyphenyl)(diphenyl)methyl residue. This fully protected compound, 3 , was submitted to a Mitsunobu reaction with the N ‐hydroxysuccinimide (NHS) ester, 5 , of (2 E )‐10‐hydroxydec‐2‐enoic acid ( 4 ) which gave nucleolipid 6 . The latter was detritylated with Cl 2 CHCOOH to yield the co‐drug 7 as NHS ester.