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Synthesis of DL-[2-14C]octan-2-sulphate and [35S]-labelled D(+)-and L(−)-octan-2-sulphate

✍ Scribed by James L. Maggs; Anthony H. Olavesen; Colin T. James

Publisher
John Wiley and Sons
Year
1980
Tongue
French
Weight
284 KB
Volume
17
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

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.

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