325957-60-6

Upstream product

• 917-64-6 methyl magnesium iodide 
• 79271-56-0 triethylsilyl trifluoromethyl sulfonate 
• 681180-44-9 methyl (5S)-5-[(1S,3aS,4S,7aS)-7a-methyl-4-(phenylsulfonyl)octahydro-1H-inden-1-yl]hexanoate 
• 66613-24-9 (phenylsulfanyl)methyl vinyl ketone 
• 681180-40-5 (1S,5R,7aS)-7a-methyl-4-phenylsulfonyl-1-{(1S)-2-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]-1-(tosyloxymethyl)ethyl}-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol 
• 343969-50-6 (1S,5R,7aS)-7a-methyl-4-phenylthio-1-{(1S)-2-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]-1-(tosyloxymethyl)ethyl}-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol 
• 325957-58-2 (S)-2-((1S,3aS,4S,7aS)-4-Benzenesulfonyl-7a-methyl-octahydro-inden-1-yl)-6-methyl-6-triethylsilanyloxy-heptan-1-ol 
• 244241-61-0 (1S,3aS,4S,7aS)-(4-benzenesulfonyl-7a-methyl-octahydro-inden-1-yl)-acetic acid ethyl ester 
• 244241-66-5 (7aR)-4-benzenesulfonyl-7a-methyl-2,3,7,7a-tetrahydro-6H-indene-1,5-dione 
• 244241-59-6 (3aS,4S,7aR)-4-benzenesulfonyl-7a-methyl-octahydro-inden-1-one 
• 244241-69-8 (7aR)-7a-methyl-4-phenylsulfanyl-2,3,7,7a-tetrahydro-6H-indene-1,5-dione 
• 681180-39-2 (1S,5R,7aS)-1-{(1S)-1-(hydroxymethyl)ethyl-2-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]}-7a-methyl-4-phenylthio-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol 
• 343969-51-7 (4S)-2,2,5,5-tetramethyl-4-{(2S)-2-[(1S,3aS,4S,7aS)-7a-methyl-4-(phenylsulfonyl)octahydro-1H-inden-1-yl]propyl}-1,3-dioxolane 
• 681180-43-8 (3S,5S)-2-methyl-5-[(1S,3aS,4S,7aS)-7a-methyl-4-(phenylsulfonyl)octahydro-1H-inden-1-yl]hexane-2,3-diol 

Relevant academic research and scientific papers

Synthesis and biological activity of the 1α,25-dihydroxyvitamin D3 diastereomer with unnatural configuration at the rings C/D side-chain moiety

1α,25-Dihydroxyvitamin D3 diastereomer, differing from the parent compound in configuration at four asymmetric carbon atoms in the rings C/D and side chain (C13, C14, C17 and C20), was synthesized and shown to have a significant affinity for the vitamin D receptor. (C) 2000 Elsevier Science Ltd.

The first synthesis and biological testing of the enantiomer of 1α,25-dihydroxyvitamin D3

The 1α,25-dihydroxyvitamin D3 enantiomer was synthesized and examined in biological tests. The ring A precursor was prepared from vitamin D2 employing the Mitsunobu reaction for inversion of the configuration at C-3 and SeO2 hydroxylation at C-1. The CD rings-side chain portion was synthesized from an optically active hexanoic acid derivative using diastereoselective tandem Mukaiyama-Michael addition and vinylsulfone reduction as the key steps. The ring A and CD rings building blocks were combined using the Julia alkenylation reaction. 1α,25-Dihydroxyvitamin D3 enantiomer shows no significant affinity to the vitamin D receptor.