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

Chinese Journal of Applied Chemistry ›› 1989, Vol. 0 ›› Issue (4): 50-53.

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

Zhang Gongcheng, Tan Zhen, Wei Shujuan, Li Yulin

Laboratory of Applied Organic Chemistry, Lanzhou University

Received:1988-08-08 Revised:1988-11-18 Published:1989-08-10 Online:1989-08-10

Abstract

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

Key words: Biomarkers, 5α-Cholestane, 5β-Cholestane, Organic synthesis

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, 0(4): 50-53.

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

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