27460-28-2

Upstream product

• 98-88-4 benzoyl chloride 
• 55573-92-7 24-hydroxycholesterol benzoate 
• 5255-17-4 3β-hydroxy-5-cholenoic acid 
• 78216-63-4 (24R)-3β,24-dihydroxycholesta-5,25-diene 3-(tetrahydropyran-2-yl) ether 
• 88156-15-4 (24R)-3β,24-dihydroxycholesta-5,25-diene 
• 78191-96-5 3β-tetrahydropyranyloxycholesta-5,25-dien-24-one 
• 66414-43-5 3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-ol 
• 58497-26-0 24-oxo-3β-cholesteryl benzoate 
• 114530-77-7 24,25-epoxycholesterol benzoate 
• 78191-95-4 3β,24-dihydroxycholesta-5,25-diene 3-(tetrahydropyran-2-yl) ether 
• 84529-74-8 (20R)-3β-(tert-butyldimethylsilyloxy)-24-oxo-25,26,27-trisnorcholest-5-ene 
• 82332-05-6 (24R)-3β,24-dibenzoyloxycholesta-5,25-diene 

Relevant academic research and scientific papers

Stereoselective Introduction of Hydroxy-groups into the 24-, 25-, and 26-Positions of the Cholesterol Side Chain

Asymmetric reduction of steroidal 25-en-24-ones by a complex of LiAlH4 and 2,2'-dihydroxy-1,1'-binaphthyl led to a stereoselective introduction of hydroxy-groups into the 24-, 25-, and 26-positions of the cholesterol side chain.

Stereochemistry of reduction of the C-24,25 double bond in the conversion of desmosterol into cholesterol

Feeding of the chemically prepared [24-13C, 24-2H]desmosterol to cell-free systems derived from rat liver and silkworm gut and to cultured cells of Oryza sativa followed by deuterium-decoupled 1H, 13C shift correlation NMR analysis of the biosynthesized cholesterol revealed the stereospecific incorporation of hydrogen atoms from the re-face of the C-24 position of desmosterol.

Stereoselective Introduction of Hydroxy Groups into the Cholesterol Side Chain. Preparation of (24R)- and (24S)-24,25-Dihydroxy- and (25R)- and (25S)-25,26-Dihydroxyvitamin D3 by Asymmetric Synthesis

24,25-Epoxy-26-hydroxy-3β-tetrahydropyranyloxycholest-5-enes (7a) and (8a), prepared by asymmetric epoxidation of the allylic alcohol (4), and 24-hydroxy-3β-tetrahydropyranyloxycholesta-5,25-dienes (11) and (12), synthesized by asymmetric reduction of the enone (6), were stereoselectively converted into 25,26-and 24,25-dihydroxycholesterol derivatives, which could be transformed into 25,26- and 24,25-dihydroxyvitamin D3.The highly stereoselective epoxide cleavage of 26-benzoyloxy-24,25-epoxides (7b), (8b), (25), and (26) was found to proceed with retention at C-24.