One-Pot Deuteration and Reduction of Ketones in the Synthesis of [16,16,17-2H3]-Epitestosterone

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Title:One-Pot Deuteration and Reduction of Ketones in the Synthesis of [16,16,17-2H3]-Epitestosterone
Creators:
Chodounská, Hana
Kasal, Alexander
Šaman, David
Ubik, Karel
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 61, 7, pp. 1037-1046
Uncontrolled Keywords:Steroid synthesis, Labelled epitestosterone

Abstract

5α-Androstan-17-one and 6β-methoxy-3α,5-cyclo-5α-androstan-17-one were reduced by sodium in deuterium oxide to [16,16,17-<sup>2</sup>H<sub>3</sub>]-17β-alcohols. The 17β-tosyloxy group of [16,16,17-<sup>2</sup>H<sub>3</sub>]-6β-methoxy-3α,5-cyclo-5α-androstan-17β-ol tosylate was found to be stable under the conditions of the i-steroid rearrangement. The S<sub>N</sub>2 reaction of the 17β-tosyloxy group with potassium nitrite yielded the corresponding 17α-hydroxy derivative without any loss of deuterium.

Title:One-Pot Deuteration and Reduction of Ketones in the Synthesis of [16,16,17-2H3]-Epitestosterone
Creators:
Chodounská, Hana
Kasal, Alexander
Šaman, David
Ubik, Karel
Uncontrolled Keywords:Steroid synthesis, Labelled epitestosterone
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:61
Number:7
Page Range:pp. 1037-1046
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19961037UNSPECIFIED
ID Code:1007
Item Type:Article
Deposited On:06 Feb 2009 17:05
Last Modified:06 Feb 2009 16:05

Citation

Chodounská, Hana; Kasal, Alexander; Šaman, David; Ubik, Karel (1996) One-Pot Deuteration and Reduction of Ketones in the Synthesis of [16,16,17-2H3]-Epitestosterone. Collection of Czechoslovak Chemical Communications, 61 (7). pp. 1037-1046. ISSN 0010-0765

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