55812-80-1

Usage

Uses

Used in Pharmaceutical Industry:
Windaus Ketone is used as an intermediate for the production of Vitamin D derivatives, which are essential for various biological functions, including calcium and phosphorus homeostasis, bone metabolism, and immune system regulation. Its role in the synthesis process is crucial for the development of these vital compounds.
Windaus Ketone is also used as a chemical precursor in the synthesis of other steroidal compounds, further expanding its applications in the pharmaceutical and chemical industries. Its versatility as a starting material for various chemical reactions highlights its importance in the development of new drugs and therapeutic agents.

Upstream product

• 50-14-6 Calciferol 
• 84985-78-4 (3S,5Z,7Ξ)-9,10-seco-8ξ-ergosta-5,10(19),22t-triene-3,7,8-triol 
• 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 
• 131852-63-6 (5Z,22E)-(7R)-3β-(tert-butyldimethylsilyloxy)-9,10-seco-8α-ergosta-5,10(19),22-triene-7,8-diol 

Downstream Products

• 67337-15-9 <(1Z),(5S)>-2-<5-hydroxy-2-methylcyclohexylidene>-ethanol 
• 55812-82-3 (1R,3aR,4S,7aR)-7a-methyl-1-<(2E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl>-octahydro-1H-inden-4-ol 
• 99598-71-7 (1R,3aS,5S,7aR)-7a-Methyl-5-((S)-1-methyl-4-oxo-cyclohex-2-enyl)-1-((Z)-(R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-one 
• 99598-73-9 (1R,2S,5S)-5-Methoxymethoxy-2-methyl-2-[(1R,3aS,5S,7aR)-7a-methyl-4-oxo-1-((Z)-(R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-5-yl]-cyclohexanecarbonitrile 
• 99598-74-0 (1R,2S,5S)-2-[(1R,3aS,4S,5S,7aR)-4-Hydroxy-7a-methyl-1-((Z)-(R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-5-yl]-5-methoxymethoxy-2-methyl-cyclohexanecarbonitrile 
• 99598-72-8 (1R,2S)-2-Methyl-2-[(1R,3aS,5S,7aR)-7a-methyl-4-oxo-1-((Z)-(R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-5-yl]-5-oxo-cyclohexanecarbonitrile 
• 33813-75-1 (1R,3aR,4S,7aR)-7a-methyl-1-<(1R,4S)-1,4,5-trimethylhexyl>-octahydro-1H-inden-4-ol 
• 58322-11-5 (3aR)-7-oxo-3ar-methyl-3c-((1R:4S)-1.4.5-trimethyl-hexyl)-(7acH)-hexahydro-indan 
• 143060-73-5 10(R),19-dihydro-(5E)-3-epivitamin D₂ 
• 116329-68-1 (1R,5R,7aR)-5-((S)-4-Methoxy-1-methyl-cyclohexa-2,4-dienyl)-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-1,2,5,6,7,7a-hexahydro-inden-4-one 
• 116329-69-2 (1R,5R,7aR)-7a-Methyl-5-((S)-1-methyl-4-oxo-cyclohex-2-enyl)-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-1,2,5,6,7,7a-hexahydro-inden-4-one 
• 247900-07-8 (7Z)-Vitamin D₂ 
• 50-14-6 Calciferol 
• 142980-94-7 dihydrotachysterol₂ tert-butyldimethylsilyl ether 

Relevant academic research and scientific papers

Probing the structural requirements for vitamin D3 inhibition of the hedgehog signaling pathway

A structure-activity relationship study to elucidate the structural basis for hedgehog (Hh) signaling inhibition by vitamin D3 (VD3) was performed. Functional and non-functional regions of VD3 and VD2 were obtained through straightforward synthetic means

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 modified Julia olefination in vitamin D2 synthesis

A partial synthesis of vitamin D2 employing fragments derived from a new improved degradation procedure is described. The 7,8-double bond of the vitamin D triene system was synthesised via the modified Julia olefination. The new procedure is more efficient than the classical Julia olefination.

On the Julia Alkenylation reaction in vitamin D synthesis. Isolation of four geometrical isomers of vitamin D4

Coupling of sulfone 2 and aldehyde 3b using the Julia alkenylation procedure has been reexamined using modern product separation techniques. It was found that vitamin D4 1b and its geometric isomers 10, 11 and 12 are formed in a ratio of 75:10:10:5, respectively. The building blocks 2 and 3b were prepared from vitamin D2. Correlations for the structure assignment of vitamin D stereoisomers by 1H NMR spectroscopy are presented.