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Synthesis of (25S)‐5α‐cholestane‐3β, 26‐DIOL[2,4,2′,4′‐ 3 H 4 ]
Author(s) -
Bovara Roberto,
Longhi Renato,
Nicotra Francesco,
Vecchio Giuseppe
Publication year - 1977
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580130318
Subject(s) - chemistry , cholestane , diol , tritium , derivative (finance) , medicinal chemistry , stereochemistry , organic chemistry , financial economics , economics , physics , nuclear physics
(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 .