1934
DOI: 10.1002/hlca.193401701170
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Zur Kenntnis der Sexualhormone II. Über die Synthese des Testikelhormons (Androsteron) und Stereoisomerer desselben durch Abbau hydrierter Sterine

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Cited by 91 publications
(4 citation statements)
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“…4H NMR spectroscopy showed the intermediate 6 derived from 2 to have incorporated both the steroid and triphenylphosphine moieties in a 1:1 ratio, with no incorporation of diethyl azodicarboxylate derived fragments. The stereochemistry at the steroid carbinol carbon remained unchanged from that of the starting alcohol 2, as shown by the half bandwidth of the 3/3 (axial) hydrogen (20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30); however, the 3 H resonance was shifted downfield to approximately 4.5 ppm, in agreement with the literature9 value of 4.35 ppm for the corresponding proton in (cyclohexyloxy)triphenylphosphonium triflate. The corresponding intermediate isolated from the reaction of 3/3-cholestanol ( 7) was shown to be a phosphonium salt by the 31P NMR resonance at +59.2 ppm (CD-Cl3), in good agreement with that observed in the above NMR studies.…”
mentioning
confidence: 99%
“…4H NMR spectroscopy showed the intermediate 6 derived from 2 to have incorporated both the steroid and triphenylphosphine moieties in a 1:1 ratio, with no incorporation of diethyl azodicarboxylate derived fragments. The stereochemistry at the steroid carbinol carbon remained unchanged from that of the starting alcohol 2, as shown by the half bandwidth of the 3/3 (axial) hydrogen (20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30); however, the 3 H resonance was shifted downfield to approximately 4.5 ppm, in agreement with the literature9 value of 4.35 ppm for the corresponding proton in (cyclohexyloxy)triphenylphosphonium triflate. The corresponding intermediate isolated from the reaction of 3/3-cholestanol ( 7) was shown to be a phosphonium salt by the 31P NMR resonance at +59.2 ppm (CD-Cl3), in good agreement with that observed in the above NMR studies.…”
mentioning
confidence: 99%
“…The 5B-cholestan-3-one was isolated by means of preparative thin layer chromatography with Kieselgel G (Merck, Darmstadt, Germany) as adsorbent and benzene-ethyl acetate (85: 15, v/v), as solvent. Crystallization from a methanol-ethyl acetate mixture yielded 26 mg of [4B-3H,4-14C]5B-cholestan-3-one, m. p. 58", reported m. p. 61-62' [13]. The ratio of 3H to 14C was 2.7 ( Table 2).…”
Section: Methodsmentioning
confidence: 99%
“…184-185°, [<*]" +95°(ethanol), vm»x. 1736 cm.-1 and free hydroxyl band; reported (9): m.p. 182-183°, [a]" +94.6°(ethanol).…”
Section: Experimental4unclassified
“…However, when epiandrosterone p-toluenesulfonate (lb) [prepared (5) from isoandrosterone (la) in over 90% yield] was treated with sodium acetate in boiling acetic acid and acetic anhydride, it was converted to a mixture which was resolved readily by silica chromatography into A2-androsten-17-one (III) as major component (54 %)2 and androsterone acetate (Ila) as minor component (39%).3 The latter could be saponified quantitatively to androsterone (lib). The structures assigned to these substances follow from the elementary analyses, infrared spectra and the similarity of physical properties to those of the known compounds (1,7,9). Since A2-androsten-17-one (III) was the major product formed in the acetolysis step and changing the reaction conditions did not appreciably alter the ratio of III to Ila, it was highly desirable to effect the conversion of this A2-compound to androsterone.…”
mentioning
confidence: 99%