112849-26-0

Basic information

• Product Name: (5E,24R)-1,3-Bis-O-(tert-ButyldiMethylsilyl)-calcipotriene
• Synonyms: (5E,24R)-1,3-Bis-O-(tert-ButyldiMethylsilyl)-calcipotriene;1,3-bi-TBS-trans-Calcipotriol
• CAS NO: 112849-26-0
• Molecular Formula: C₃₉H₆₈O₃Si₂
• Molecular Weight: 641.12642
• Product Categories: Chiral Reagents, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 112849-26-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: (5E,24R)-1,3-Bis-O-(tert-ButyldiMethylsilyl)-calcipotriene(CAS DataBase Reference)
• NIST Chemistry Reference: (5E,24R)-1,3-Bis-O-(tert-ButyldiMethylsilyl)-calcipotriene(112849-26-0)
• EPA Substance Registry System: (5E,24R)-1,3-Bis-O-(tert-ButyldiMethylsilyl)-calcipotriene(112849-26-0)

Safety Data

• Hazardous Substances Data: 112849-26-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(5E,24R)-1,3-Bis-O-(tert-ButyldiMethylsilyl)-calcipotriene is used as an intermediate in the synthesis of MC 903, a biologically active vitamin D3 analogue. (5E,24R)-1,3-Bis-O-(tert-ButyldiMethylsilyl)-calcipotriene plays a crucial role in the development of pharmaceuticals targeting various health conditions, given the therapeutic potential of vitamin D3 analogues.
Used in Research and Development:
In the field of research and development, (5E,24R)-1,3-Bis-O-(tert-ButyldiMethylsilyl)-calcipotriene is utilized for studying the properties and effects of vitamin D3 analogues. This helps scientists and researchers to understand their mechanisms of action and potential applications in medicine.

Upstream product

• 565429-98-3 C₄₁H₇₀O₄Si₂ 
• 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 
• 112849-15-7 (2-cyclopropyl-2-oxoethyl) (triphenyl)phosphonium bromide 
• 87680-65-7 (S)-3-[(1R,3aS,7aR)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-5-ol 
• 112828-12-3 3(R)-(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5(Z),7(E),10⁽¹⁹⁾-triene 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 7691-76-1 1-cyclopropyl-2-(triphenyl-λ⁵-phosphanylidene)ethan-1-one 
• 69267-75-0 2-bromo-1-cyclopropylethan-1-one 
• 765-43-5 Cyclopropyl methyl ketone 
• 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 
• 878285-87-1 SO₂-adduct of 1(S),3(R)-bis(tert-butyl-dimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'(R)-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10⁽¹⁹⁾-triene 
• 87417-26-3 (3S,6S)-(tert-butyldimethylsilyloxy)-9,10-seco-ergosta-5,7(E),10⁽¹⁹⁾,22(E)-tetraene SO₂-adduct 
• 87417-26-3 (3S,6R)-(tert-butyldimethylsilyloxy)-9,10-seco-ergosta-5,7(E),10⁽¹⁹⁾,22(E)-tetraene SO₂ adduct 
• 87422-13-7 3(S)-tert-butyldimethylsilyloxy-20(S)-formyl-9,10-secoprega-5,7(E),10⁽¹⁹⁾-triene 

Downstream Products

• 112910-41-5 (1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(R)-cycloprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10⁽¹⁹⁾-triene 
• 115540-29-9 (1S,3R,1'S,2'S,3'R)-(3'-cyclopropyl-1',2'-epoxy-3'-hydroxypropyl)-9,10-secopregna-5(E),7(E),10⁽¹⁹⁾-triene 
• 115540-29-9 (1S,3R,1'R,2'R,3'R)-(3'-cyclopropyl-1',2'-epoxy-3'-hydroxypropyl)-9,10-secopregna-5(E),7(E),10⁽¹⁹⁾-triene 
• 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 
• 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 

Relevant articles and documents

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.

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.