343969-45-9

Upstream product

• 98-98-6 2-Picolinic acid 
• 84985-78-4 (4R,7aR)-1-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-4-((R,Z)-1-hydroxy-2-((S)-5-hydroxy-2-methylenecyclohexylidene)ethyl)-7a-methyloctahydro-1H-inden-4-ol 
• 50-14-6 Calciferol 
• 343969-43-7 Pyridine-2-carboxylic acid (R)-3-[(R)-2-hydroxy-2-[(1R,3aR,4R,7aR)-4-hydroxy-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-yl]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester 

Downstream Products

• 343969-42-6 (2Z)-[(3R,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methylenecyclohexylidene]acetaldehyde 
• 338956-81-3 (Z,3R,5S)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol 
• 343969-47-1 (1R,3aR,4R,7aR)-4-{(R)-2-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-1-hydroxy-ethyl}-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-ol 
• 343969-46-0 (1R,3aR,4R,7aR)-4-{(R)-2-[(3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-2-methylene-cyclohex-(Z)-ylidene]-1-hydroxy-ethyl}-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-ol 

Relevant academic research and scientific papers

Synthesis of the enantiomer of 1α,25-dihydroxy vitamin D3 (calcitriol) and a diastereomer of 1α,25-dihydroxy vitamin D3 differing from natural product in configuration at all but one asymmetric carbon atoms

Convergent synthesis of ent-1α,25-dihydroxyvitamin D3 (ent-calcitriol, 2) and (1S,3S, 13S,14S,17S,20S) - 1α,25-dihydroxyvitamin D3 (5) using the ring A building blocks, 6 and 7, respectively, and rings CD building block 8, is describ

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.