Syntheses of deuterium labeled bile alcohols

✍ Scribed by Kenji Kihira; Daisaku Kosaka; Mizuho Une; Toshihito Hiraoka; Goro Kajiyama; Takahiko Hoshita

• Publisher: John Wiley and Sons
• Year: 1987
• Tongue: French
• Weight: 319 KB
• Volume: 24
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580241203

✦ Synopsis

5B-cholestane-3a,7a,12a,23,25p e n t o l e x h i b i t e d t h e f r a g m e n t i o n a t m/z 131 a s t h e b a s e i o n , a n d o t h e r i o n s o b s e r v e d were q u i t e weak (less t h a n 5% c o m p a r e t o t h e b a s e i o n ) i n t h e i r mass s p e c t r a analyzed as t r i m e t h y l s i l y l (TMS) e t h e r s (1,12). The base i o n a t m/z 131 c o n s i s t e d of t h e (CH3)2C(YTMS moiety due t o t h e s c i s s i o n of t h e bond between C24 and C25. Therefore, d e u t e r i u m were introduced a t C26 and C27. Methyl 3a,7a,12atrihydroxy-25-homo-5f3-cholan-25-oate (1) was t r e a t e d w i t h CD3MgI t o y i e l d [ 26,27-D6]56-cholestane-~,7a,12a,25-tetro1 u. By t h e similar r o u t e , (238)-5& cholestane-3a,7a,l2a,23,25-pentol was l a b e l e d w i t h d e u t e r i u m a t C26 and C27. M e t h y l (23S)-3a,7a,12~,23-tetrahydroxy-25-homo-5~-cholan-25-oate (6b) was p r e p a r e d from 3a,7a,l2a-triacetoxy-24-nor-58-cholan-23-a1 ( 5 J by Reformatsky