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Synthesis and Spectroscopic Characterization of Dimeric Steroidal Oximes

✍ Scribed by Duddeck, Helmut ;Frelek, Jadwiga ;Snatzke, Günther ;Szczepek, Wojciech J. ;Wagner, Petra

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
365 KB
Volume
1992
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Hydrolysis of 3β‐5‐diacetoxy‐5β‐cholestan‐6‐one oxime (1) gave seven products which, in addition to 3β‐acetoxy‐ and (6__E__)‐3β‐hydroxy‐5‐methoxy‐5α‐cholestan‐6‐one oxime (3 and 4), are identified as the dimeric steroids (6__E__,6′E)‐6‐(6′‐hydroxyimino‐5′α‐cholestan‐5′‐yl‐oximino)cholestanes 6–10. On the other hand, the 3α epimer 3α,5‐diacetoxy‐5β‐cholestan‐6‐one oxime (2) afforded the monomeric (6__E__)‐3α‐hydroxy‐5‐methoxy‐5α‐cholestan‐6‐one oxime (5) and (6__E__)‐3α‐hydroxy‐4‐cholesten‐6‐one oxime (11) only. All new compounds are characterized by NMR and MS methods. The CD spectra of 1–12 are documented.

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## Abstract Reaction of 5__α__‐cholestan‐6‐one oxime (**1**), its 3__β__‐acetoxy and 3__β__‐chloro analogs, **2** and **3**, respectiveley, with ClCH~2~CH~2~NH~2~⋅HCl in presence of MeONa afforded 6‐[(2‐aminoethoxy)imino]‐5__α__‐cholestane (**4**), 3__β__‐acetoxy‐6‐[(2‐aminoethoxy)imino]‐5__α__‐cho