Complete assignments of the 1H and 13C NMR spectra of testosterone and 17α-methyltestosterone and the 1H parameters obtained from 600 MHz spectra

✍ Scribed by Kikuko Hayamizu; Osamu Kamo

• Publisher: John Wiley and Sons
• Year: 1990
• Tongue: English
• Weight: 516 KB
• Volume: 28
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/mrc.1260280311

✦ Synopsis

Abstract

Complete sets of ^1^H chemical shifts and spin coupling constants of testosterone and 17α‐methyltestosterone were determined by analysis of the 600 MHz ^1^H NMR spectra. The spin coupling constants of the two compounds have similar values, but the substitution of a methyl group at the 17α‐position changes the ^1^H chemical shifts of some protons on the C and D rings: low‐field shifts for H‐12α, H‐14α and H‐16α and high‐field shifts for H‐12β and H‐16β. The two‐dimensional ^1^H‐^1^H COSY and NOESY methods were used for unambiguous assignments, including those for the signals of H‐16α and H‐16β which are interchanged in the present paper from the assignment reported previously. Two‐dimensional ^1^H‐^13^C shift correlated spectroscopy was also used to complement the ^1^H and ^13^C assignments. The effect on the ^13^C chemical shifts of methyl substitution at the 17α‐position is briefly discussed.