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Citation: Zhang Gongcheng, Tan Zhen, Wei Shujuan, Li Yulin. SYNTHESIS 0F BI0MARKERS Ⅲ. SYNTHESIS OF 5α-CHOLESTANE AND 5β-CHOLESTANE[J]. Chinese Journal of Applied Chemistry, ;1989, 6(4): 50-53. shu

SYNTHESIS 0F BI0MARKERS Ⅲ. SYNTHESIS OF 5α-CHOLESTANE AND 5β-CHOLESTANE

1.
Laboratory of Applied Organic Chemistry, Lanzhou University

Received Date: 8 August 1988
Available Online: 18 November 1988

In this paper the synthesis of 5α-cholestane 4 and 5β-cholestane 7 from cholesterol by means of stereospecific reaction is reported. Cholesterol 1 was first converted into 5α-dihydrocholesterol 2 by stercoselective catalytic hydrogenation, then into 5α-cholestane 4 by successive oxidation with PDC and Clemmensen reduction. 5β-Cholestane 7 was synthesized by Oppenauer oxidation of chole-sterol to 4-cholesten-3-one 5, following by stereoselective catalytic hydrogenation and Clemmensen reduction. In above reactions the stereoselective catalytic hydrogenation was a key step. The structure and configuration of the intermediates and target molecules were confirmed by their GC, MS, ORD and CD data.
- Biomarkers,
- 5α-Cholestane,
- 5β-Cholestane,
- Organic synthesis
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