332950-57-9

Upstream product

• 343969-48-2 S-tert-butyl (2S)-[(1S,2S)-3-oxo-2-(3-oxo-4-phenylthiobutyl)cyclopentyl-]-3-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]propanethioate 
• 332950-54-6 S-tert-butyl 3-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]propanethioate 
• 66613-24-9 (phenylsulfanyl)methyl vinyl ketone 

Downstream Products

• 332950-58-0 S-tert-butyl (2S)-2-[(1S,5R,7aS)-5-hydroxy-7a-methyl-4-phenylthio-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl]-3-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]propanethioate 
• 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 
• 325957-60-6 [(S)-5-((1S,3aS,4S,7aS)-4-Benzenesulfonyl-7a-methyl-octahydro-inden-1-yl)-1,1-dimethyl-hexyloxy]-triethyl-silane 
• 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 
• 343969-52-8 methyl (2E,5S)-5-[(1S,3aS,4S,7aS)-7a-methyl-4-(phenylsulfonyl)octahydro-1H-inden-1-yl]hex-2-enoate 
• 681180-44-9 methyl (5S)-5-[(1S,3aS,4S,7aS)-7a-methyl-4-(phenylsulfonyl)octahydro-1H-inden-1-yl]hexanoate 

Relevant academic research and scientific papers

1,3- versus 1,4-Asymmetric induction in Mukaiyama-Michael additions of optically active ketene acetals to 2-methylcyclopent-2-en-1-one: A remarkable inversion of facial selectivity

TrSbCl6-catalyzed addition of selected optically active ketene acetals to 2-methylcyclopent-2-en-1-one for steroid synthesis is described. Inversion of facial selectivity in 1,3- and 1,4-asymmetric induction was observed.

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.