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Synthesis of (25S)-5α-cholestane-3β, 26-DIOL[2,4,2′,4′-3H4]

✍ Scribed by Roberto Bovara; Renato Longhi; Francesco Nicotra; Giuseppe Vecchio


Publisher
John Wiley and Sons
Year
1977
Tongue
French
Weight
308 KB
Volume
13
Category
Article
ISSN
0022-2135

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✦ Synopsis


Abstract

(25S)–5α‐cholestane‐3β, 26‐diol [2,4,2′,4′–^3^H~4~] was synthesized by hydrogenation of neotigogenin acetate 2, followed by acetylation to (25S)‐5α‐furostane‐3β, 26‐diol diacetate 5; this was oxidized to (25S)–16–22‐dioxo‐5α‐cholestane‐3β, 26‐diol diacetate 6. Clemmensen reduction of the last product afforded (25S)–5α‐cholestane‐3β, 26‐diol 26‐monoacetate 9, which was oxidized to 3‐oxo‐derivative 12; this was tritium labelled by base‐catalyzed exchange with 0.1 N‐NaOH in iso PrO^3^H and reduced to 14 with NaBH~4~.


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