4a-(3H )Methy1-5a-cholestan-38-01 was r e g i o s e l e c t i v e l y prepared from 5a-cho?est-I-en-3-one v i a a l k y l a t i o n with methyl i o d i d e , hydrogenation, and LAH reduction. The f i n a l and intermediate products were c h a r a c t e r i s e d by spectroscopic methods. Regio-contr
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
No coin nor oath required. For personal study only.
✦ 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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