910133-69-6

Usage

Uses

Used in Pharmaceutical Research:
9,10-Secochola-5,7,10(19),22-tetraen-24-ol, 24-cyclopropyl-1,3-bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-, (1α,3β,5Z,7E,24S)(9CI) is used as a research compound in pharmaceutical research for its potential applications in the development of new drugs and therapeutic agents. Its unique structure and reactivity may offer novel opportunities for drug discovery and design.
Used in Organic Chemistry:
In the field of organic chemistry, 9,10-Secochola-5,7,10(19),22-tetraen-24-ol, 24-cyclopropyl-1,3-bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-, (1α,3β,5Z,7E,24S)(9CI) serves as a valuable intermediate or building block for the synthesis of more complex organic molecules. Its specific functional groups and structural features can be exploited in various chemical reactions and transformations.
Used in Material Science:
9,10-Secochola-5,7,10(19),22-tetraen-24-ol, 24-cyclopropyl-1,3-bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-, (1α,3β,5Z,7E,24S)(9CI) has potential applications in material science, where its unique structure and properties can be utilized in the development of new materials with specific characteristics. Further studies and experiments are needed to explore its potential uses in various material science applications.

Upstream product

• 112849-26-0 (1S,3R,3'R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10⁽¹⁹⁾-triene 
• 765-43-5 Cyclopropyl methyl ketone 
• 69267-75-0 2-bromo-1-cyclopropylethan-1-one 
• 7691-76-1 1-cyclopropyl-2-(triphenyl-λ⁵-phosphanylidene)ethan-1-one 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 87407-47-4 3(S)-tert-butyldimethylsilyloxy-20(S)-formyl-9,10-secoprega-5,7(E),10⁽¹⁹⁾-triene 
• 87422-13-7 3(S)-tert-butyldimethylsilyloxy-20(S)-formyl-9,10-secoprega-5,7(E),10⁽¹⁹⁾-triene 
• 87417-26-3 (3S,6R)-(tert-butyldimethylsilyloxy)-9,10-seco-ergosta-5,7(E),10⁽¹⁹⁾,22(E)-tetraene SO₂ adduct 
• 87417-26-3 (3S,6S)-(tert-butyldimethylsilyloxy)-9,10-seco-ergosta-5,7(E),10⁽¹⁹⁾,22(E)-tetraene SO₂-adduct 
• 112849-17-9 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3’-cyclopropyl-3’-oxypropyl-1’(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene 
• 112849-27-1 (1S,3R,3'S)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10⁽¹⁹⁾-triene 
• 590366-68-0 C₃₅H₆₀O₂Si₂ 
• 1489-69-6 Cyclopropanecarboxaldehyde 
• 112828-12-3 3(R)-(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5(Z),7(E),10⁽¹⁹⁾-triene 

Downstream Products

• 112827-99-3 20(R)-(3'(R)-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-1(S),3(R)-dihydroxy-9,10-secopregna-5(Z),7(E),10⁽¹⁹⁾-triene 

Relevant academic research and scientific papers

Stereoselective synthesis of C24-hydroxylated vitamin D3 analogs: A practical and expeditius route to calcipotriol

The synthesis of the clinically important drug calcipotriol (2, MC903) is described as an example of a new and efficient approach to C24-hydroxylated analogs and metabolites of vitamin D3 (1). The key step of the process is the generation of the C24 stereocenter by DAIB [(-)-3-exo-(dimethylamino)isoborneol]-catalyzed addition of the alkenylzinc derivative of alkyne 3 to cyclopropylcarboxaldehyde.

EPIMERIZATION BY STEREOSELECTIVE SYNTHESIS OF VITAMIN D ANALOGUES

A method for epimerization process of C-24 ketones to desired C-24 alcohol by stereo selective reduction using chiral borane reducing agents in the presence of chiral auxillary such as (R)-2-methyl-CBS-oxazaborolidine for the preparation of calcipotriene intermedites and its process to calcipotriene.

ISOMERISATION OF PHARMACEUTICAL INTERMEDIATES

The present invention relates to an isomerisation method of vitamin D analogues, such as compounds useful for the synthesis of calcipotriol, and to and to the use of a flow- through photoreactor or continuous flow photoreactor reactor for making said vitamin D analogues. The present invention relates further to the use of intermediates produced with said method for making calcipotriol or calcipotriol monohydrate, or pharmaceutical formulations thereof.

EPIMERISATION OF ALLYLIC ALCOHOLS

The present invention relates to processes for epimerising alcohols of compounds having a hydroxyl substituent on an asymmetric allylic carbon, such as compounds useful for the synthesis of vitamin D analogues where the epimeric hydroxyl substituent is at the 24 position. The invention further relates to methods of producing intermediates useful for the synthesis of calcipotriol by said epimerisation processes.

STEREOSELECTIVE SYNTHESIS OF VITAMIN D ANALOGUES

The present invention relates to intermediates useful for the synthesis of calcipotriol or calcipotriol monohydrate, to methods of producing said intermediates, and to methods of stereoselectively reducing said intermediates.

EPIMERIZATION OF ANALOGS OF VITAMIN D

Provided is a method of general applicability of epimerizing a vitamin-D analog having an asymmetric allylic carbon atom at the C-24 position, which comprises the steps of: a) esterifying the hydroxyl group on the asymmetric allylic carbon atom at the 24 position with an esterifying agent, b) contacting a solution of the ester in a solvent with an epimerization-active solid, whereby the ester is epimerized, and c) hydrolysing the epimerized ester to obtain a mixture of C-24 epimers having a hydroxyl substituent on the asymmetric allylic carbon at position 24. The method is of particular utility in making calcipotriene.