(5E,24R)-1,3-Bis-O-(tert-ButyldiMethylsilyl)-calcipotriene

Base Information

• Chemical Name: (5E,24R)-1,3-Bis-O-(tert-ButyldiMethylsilyl)-calcipotriene
• CAS No.: 112849-26-0
• Molecular Formula: C₃₉H₆₈O₃Si₂
• Molecular Weight: 641.138
• Mol file: 112849-26-0.mol

Synonyms:(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

Chemical Property of (5E,24R)-1,3-Bis-O-(tert-ButyldiMethylsilyl)-calcipotriene

Chemical Property:

• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate

Purity/Quality:

95% ^*data from raw suppliers

(5E,24R)-1,3-Bis-O-(tert-Butyldimethylsilyl)-calcipotriene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (5E)-Calcipotriene (C144210) derivative. Intermediate in the preparation of MC 903, a biologically active vitamin D3 analogue.

Technology Process of (5E,24R)-1,3-Bis-O-(tert-ButyldiMethylsilyl)-calcipotriene

There total 22 articles about (5E,24R)-1,3-Bis-O-(tert-ButyldiMethylsilyl)-calcipotriene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 33.0%

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 (112849-17-9) → (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 (112849-26-0,134523-61-8,910133-69-6,910133-34-5) + (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 (112849-27-1,134523-61-8,910133-69-6,910133-34-5)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; further reag.: (S)-BINAL-H;

DOI:10.1016/S0040-4020(01)86903-9

Reference yield:

SO2-adduct of 1(S),3(R)-bis(tert-butyl-dimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'(S)-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene + 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 (878285-87-1) → (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 (112849-26-0,134523-61-8,910133-69-6,910133-34-5) + (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 (112849-27-1,134523-61-8,910133-69-6,910133-34-5)

Guidance literature:

With sodium hydrogencarbonate; In water; at 90 ℃; for 2 - 2.5h;

Reference yield:

C39H70O5SSi2 + C39H70O5SSi2 + C39H70O5SSi2 + C39H70O5SSi2 → (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 (112849-26-0,134523-61-8,910133-69-6,910133-34-5) + (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 (112849-27-1,134523-61-8,910133-69-6,910133-34-5)

Guidance literature:

With sodium hydrogencarbonate; In tert-butyl methyl ether; water; toluene; at 90 ℃; for 2 - 2.5h;

upstream raw materials:

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

Cyclopropyl methyl ketone

2-bromo-1-cyclopropylethan-1-one

1-cyclopropyl-2-(triphenyl-λ⁵-phosphanylidene)ethan-1-one

Downstream raw materials:

(1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(R)-cycloprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10⁽¹⁹⁾-triene

(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

(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

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