338956-81-3

Upstream product

• 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 
• 242808-65-7 ((2R,3R)-3-(2-(4-methoxybenzyloxy)ethyl)oxiran-2-yl)methanol 
• 220861-39-2 (R)-3-((tert-butyldimethylsilyl)oxy)pent-4-enal 
• 50-14-6 Calciferol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 338956-79-9 (Z,5R,7R)-bis(tert-butyldimethylsilyl)oxy-3-(trifluoromethanesulfonyl)oxy-2,8-nonadien-1-ol 
• 338956-77-7 methyl (Z,5R,7R)-bis(tert-butyldimethylsilyl)oxy-3-(trifluoromethanesulfonyl)oxy-2,8-nonadienoate 
• 338957-05-4 2,2-Dimethyl-propionic acid (3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-hept-6-enyl ester 
• 338956-75-5 methyl (5R,7R)-bis(tert-butyldimethylsilyl)oxy-3-oxo-8-nonenoate 
• 338956-73-3 methyl (5S,7R)-bis(tert-butyldimethylsilyl)oxy-3-hydroxy-8-nonenoate 
• 338956-69-7 (3S,5R)-3,5-bis(tert-butyldimethylsilyl)oxy-6-hepten-1-ol 
• 338956-71-1 (3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-hept-6-enal 
• 338956-67-5 (3S,5R)-5-(tert-butyldimethylsilyl)oxy-1-pivaloyloxy-6-hepten-3-ol 
• 338956-99-3 (R)-tert-butyl(5-(4-methoxybenzyloxy)pent-1-en-3-yloxy)dimethylsilane 

Downstream Products

• 343969-42-6 (2Z)-[(3R,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methylenecyclohexylidene]acetaldehyde 
• 338956-92-6 (5Z,7E,1R,3S,20S)-1,3-bis(tert-butyldimethylsilyloxy)-20-(3-methyl-3-trimethylsilyloxybutyloxy)-9,10-secopregna-5,7,10⁽¹⁹⁾-triene 
• 338956-85-7 (Z,3R,5S)-2-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylideneethyl]diphenylphosphine oxide 

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.

Synthesis and evaluation of A-ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D3 (OCT)

A-ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D3 (OCT) (2), 3-epi-1α,25-dihydroxy-22-oxavitamin D3 (3-epiOCT) (3) and 1,3-diepi-1α,25-dihydroxy-22-oxavitamin D3 (1,3-diepiOCT) (4) were synthesized by the convergent method. In vitro binding affinity for rat vitamin D binding protein and calf-thymus vitamin D receptor, differentiation-inducing activity on HL-60 cells, and transcriptional activity of 3-epiOCT (3) and 1,3-diepiOCT (4) were evaluated in comparison with OCT (2), 1-epi-1α,25-dihydroxy-22-oxavitamin D3 (1-epiOCT) (5) and 1α,25-dihydroxyvitamin D3 (1).