Synthesis of [3α-(3) H] 17α-hydroxy pregnenolone and [3α-(3) H] pregnenolone.
For the first time, [3α-(3) H] 17α-hydroxy pregnenolone (1) was synthesized through a multiple step sequence. The presence of [3β-(3) H] isomer in RP-HPLC purified product was identified by tritium NMR. The [3β-(3) H] isomer was then separated from [3α-(3) H] 17α-hydroxy pregnenolone with chiralPAK AD-H column. [3α-(3) H] pregnenolone (2) was synthesized from commercial available 5-pregnen-3,20-dione in one step with an improved procedure.
Radiochemical Synthesis Group, Bristol-Myers Squibb Company, Route 206 and Province Line Road, Princeton, NJ, 08543, USA.
Yuan
Y
Tian
Yang
Y
Hong
Samuel J
SJ
Bonacorsi
Aaron
A
Balog
Sharon
S
Gong
D006907:17-alpha-Hydroxypregnenolone / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D011284:Pregnenolone / Q000138:chemical synthesis* / Q000737:chemistry*; D011854:Radiochemistry; D013237:Stereoisomerism; D014316:Tritium
D014316:Tritium; D006907:17-alpha-Hydroxypregnenolone; D011284:Pregnenolone
17α-hydroxy pregnenolone; chiralPAK AD-H column; isomer; pregnenolone; tritium; tritium-NMR (T-NMR)