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

Autor:	Hana Chodounska, Karel Ubik, Alexander Kasal, David Šaman
Rok vydání:	1996
Předmět:	Sodium Epitestosterone Oxide chemistry.chemical_element General Chemistry Medicinal chemistry chemistry.chemical_compound Potassium nitrite chemistry Deuterium Steroid synthesis medicine Organic chemistry Derivative (chemistry) medicine.drug
Zdroj:	Collection of Czechoslovak Chemical Communications. 61:1037-1046
ISSN:	1212-6950 0010-0765
DOI:	10.1135/cccc19961037
Popis:	5α-Androstan-17-one and 6β-methoxy-3α,5-cyclo-5α-androstan-17-one were reduced by sodium in deuterium oxide to [16,16,17-2H3]-17β-alcohols. The 17β-tosyloxy group of [16,16,17-2H3]-6β-methoxy-3α,5-cyclo-5α-androstan-17β-ol tosylate was found to be stable under the conditions of the i-steroid rearrangement. The SN2 reaction of the 17β-tosyloxy group with potassium nitrite yielded the corresponding 17α-hydroxy derivative without any loss of deuterium.
Databáze:	OpenAIRE
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