(1S,4R,E)-4-((1R,3aS,7aR,E)-4-((Z)-2-((3S,5R)-3,5-bis((tert-butyldiMethylsilyl)oxy)-2-Methylenecyclohexylidene)ethylidene)-7a-Methyloctahydro-1H-inden-1-yl)-1-cyclopropylpent-2-en-1-ol

Base Information

• Chemical Name: (1S,4R,E)-4-((1R,3aS,7aR,E)-4-((Z)-2-((3S,5R)-3,5-bis((tert-butyldiMethylsilyl)oxy)-2-Methylenecyclohexylidene)ethylidene)-7a-Methyloctahydro-1H-inden-1-yl)-1-cyclopropylpent-2-en-1-ol
• CAS No.: 112875-61-3
• Molecular Formula: C39H68O3Si2
• Molecular Weight: 641.138
• Mol file: 112875-61-3.mol

Synonyms:1,3-Bis-O-(tert-butyldimethylsilyl)calcipotriene;(1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(S)-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10(19)-triene;UNII-4SP93VP62P;1(S),3(R)-bis(tert-butyl-dimethylsilyloxy)-20(R)-(3'-cyclopropyl-3(S)'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10(19)-triene;

Chemical Property of (1S,4R,E)-4-((1R,3aS,7aR,E)-4-((Z)-2-((3S,5R)-3,5-bis((tert-butyldiMethylsilyl)oxy)-2-Methylenecyclohexylidene)ethylidene)-7a-Methyloctahydro-1H-inden-1-yl)-1-cyclopropylpent-2-en-1-ol

Chemical Property:

• Boiling Point: 628.2±55.0 °C(Predicted)
• PKA: 14.29±0.20(Predicted)
• PSA: 38.69000
• Density: 0.98±0.1 g/cm3(Predicted)
• LogP: 11.14960

Purity/Quality:

99%min ^*data from raw suppliers

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: 1,3-Bis(O-TBDMS)-Calcipotriene is the tert-Butyldimethylsilyl ether conjugate of Calcipotriene (C144200), a vitamin D3 analogue with potential antitumor activities.

Technology Process of (1S,4R,E)-4-((1R,3aS,7aR,E)-4-((Z)-2-((3S,5R)-3,5-bis((tert-butyldiMethylsilyl)oxy)-2-Methylenecyclohexylidene)ethylidene)-7a-Methyloctahydro-1H-inden-1-yl)-1-cyclopropylpent-2-en-1-ol

There total 19 articles about (1S,4R,E)-4-((1R,3aS,7aR,E)-4-((Z)-2-((3S,5R)-3,5-bis((tert-butyldiMethylsilyl)oxy)-2-Methylenecyclohexylidene)ethylidene)-7a-Methyloctahydro-1H-inden-1-yl)-1-cyclopropylpent-2-en-1-ol 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: 63.0%

C35H60O2Si2 (590366-68-0) + Cyclopropanecarboxaldehyde (1489-69-6) → (1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(S)-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10(19)-triene (112875-61-3,134523-61-8,910133-69-6,910133-34-5)

Guidance literature:

C₃₅H₆₀O₂Si₂; With bis(cyclohexanyl)borane; diethylzinc; (2R)-3-exo-(dimethylamino)isoborneol; In hexane; at -20 - 0 ℃;

Cyclopropanecarboxaldehyde; In hexane; at 0 ℃;

DOI:10.1016/j.jsbmb.2010.03.074

Reference yield:

(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) → (1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(S)-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10(19)-triene (112875-61-3,134523-61-8,910133-69-6,910133-34-5)

Guidance literature:

With anthracene; triethylamine; In toluene; at 20 ℃; for 1h; Irradiation;

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

Reference yield:

(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) → C39H68O3Si2 + (1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(S)-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10(19)-triene (112875-61-3,134523-61-8,910133-69-6,910133-34-5)

Guidance literature:

9-acetylanthracene; In tert-butyl methyl ether; at 10 ℃; Product distribution / selectivity; UV-irradiation;

upstream raw materials:

(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

Cyclopropyl methyl ketone

2-bromo-1-cyclopropylethan-1-one

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

Downstream raw materials:

calcipotriene

Refernces

• 1、 -. "EPIMERIZATION BY STEREOSELECTIVE SYNTHESIS OF VITAMIN D ANALOGUES". Page/Page column 11-12. . Retrieved 2009/06/27.
• 2、 -. "EPIMERISATION OF ALLYLIC ALCOHOLS". Page/Page column 25. . Retrieved 2008/06/13.