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Synthesis of DL‐[2‐ 14 C]octan‐2‐sulphate and [ 35 S]‐labelled D(+)‐and L(−)‐octan‐2‐sulphate
Author(s) -
Maggs James L.,
Olavesen Anthony H.,
James Colin T.
Publication year - 1980
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580170606
Subject(s) - chemistry , methyl iodide , magnesium bromide , pyridine , lithium aluminium hydride , medicinal chemistry , iodide , bromide , heptanal , adduct , hydrolysis , wittig reaction , nuclear chemistry , organic chemistry , magnesium , aldehyde , catalysis
DL‐[2‐ 14 C]Octan‐2‐sulPhate was prepared by sulphating DL‐[2‐ 14 C]octan‐2‐ol with pyridine‐SO 3 adduct. Synthesis of the DL‐[2‐ 14 C]alkanol started with carboxylation of hexyl magnesium bromide with 14 CO 2 . Subsequent methylation with diazomethane and reduction of the ester with lithium aluminium hydride Yieled [1‐ 14 C]heptan‐1‐ol. The latter was oxidized to 1‐ 14 C heptanal with Seloxcette. The [1‐ 14 C]heptanal was reacted with methyl magnesium iodide to give DL‐[2‐ 14 C]octan‐2‐ol. D(+)‐ and L(−)‐Octan‐2‐[ 35 S]sulphate were synthesized by sulphating the stereochemically pure alcohols with pyridine‐ 35 SO 3 prepared from 35 SO 3 . These synthetic routes provided specifically radiolabelled secondary alkyl sulphates of high chemical and radiochemical purity. The identity and purity of the products was confirmed by mass spectrometry, infrared spectroscopy, t.l.c. and stereospecific enzymic hydrolysis.