(1S,5R,Z)-5-(tert-butyldiMethylsilyloxy)-3-((E)-2-((1R,3aS,7aR)-1-((R)-6-hydroxy-6-Methylheptan-2-yl)-7a-Methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-2-Methylenecyclohexanol

Base Information

• Chemical Name: (1S,5R,Z)-5-(tert-butyldiMethylsilyloxy)-3-((E)-2-((1R,3aS,7aR)-1-((R)-6-hydroxy-6-Methylheptan-2-yl)-7a-Methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-2-Methylenecyclohexanol
• CAS No.: 132054-64-9
• Molecular Formula: C33H55O3Si
• Molecular Weight: 530.907
• Mol file: 132054-64-9.mol

Synonyms:(1S,5R,Z)-5-(tert-butyldiMethylsilyloxy)-3-((E)-2-((1R,3aS,7aR)-1-((R)-6-hydroxy-6-Methylheptan-2-yl)-7a-Methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-2-Methylenecyclohexanol

Chemical Property of (1S,5R,Z)-5-(tert-butyldiMethylsilyloxy)-3-((E)-2-((1R,3aS,7aR)-1-((R)-6-hydroxy-6-Methylheptan-2-yl)-7a-Methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-2-Methylenecyclohexanol

Chemical Property:

• PSA: 49.69000
• LogP: 9.12430

Purity/Quality:

99% ^*data from raw suppliers

(1S,5R,Z)-5-(tert-butyldimethylsilyloxy)-3-((E)-2-((1R,3aS,7aR)-1-((R)-6-hydroxy-6-methylheptan-2-yl)-7a-methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-2-methylenecyclohexanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1S,5R,Z)-5-(tert-butyldiMethylsilyloxy)-3-((E)-2-((1R,3aS,7aR)-1-((R)-6-hydroxy-6-Methylheptan-2-yl)-7a-Methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-2-Methylenecyclohexanol

There total 22 articles about (1S,5R,Z)-5-(tert-butyldiMethylsilyloxy)-3-((E)-2-((1R,3aS,7aR)-1-((R)-6-hydroxy-6-Methylheptan-2-yl)-7a-Methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-2-Methylenecyclohexanol 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: 95.0%

25-hydroxy-5E-[6,19,19'-H3]vitamin D3-3β-tert-butyldimethylsilyl ether (140710-90-3) → 1α,25-dihydroxy-5E-vitamin D3-3β-tert-butyldimethylsilyl ether (132054-64-9)

Guidance literature:

25-hydroxy-5E-[6,19,19'-H3]vitamin D3-3β-tert-butyldimethylsilyl ether; With selenium(IV) oxide; In dichloromethane; for 0.5h; Reflux; Inert atmosphere;

With 4-methylmorpholine N-oxide; In dichloromethane; for 1h; stereospecific reaction; Reflux; Inert atmosphere;

DOI:10.1016/j.bmcl.2011.02.025

Reference yield: 67.0%

1α,25-dihydroxy-5E-vitamin D3-3β-tert-butyldimethylsilyl ether (132054-64-9) → 1α-[((trimethylsilyl)-oxy)]-3β-[((tertiary-butyl-dimethylsilyl)-oxy)], 25-trihydroxy-9,10-5(Z),7(E),10(19)-triene (132054-64-9)

Guidance literature:

With anthracene; triethylamine; In toluene; for 1.25h; UV-irradiation;

DOI:10.1016/j.bmcl.2011.02.025

Reference yield: 65.0%

(3-bromo-1,1-dimethylpropoxy)triethylsilane (87417-12-7) + 1α-[((trimethylsilyl)-oxy)]-3β-[((tertiarybutyl-dimethylsilyl)-oxy)]-20(S)-[[(p-tolylsulfonyl)oxy]methyl]-9,10-secopregna-5(Z),7(E),10(19)-triene → 1α-[((trimethylsilyl)-oxy)]-3β-[((tertiary-butyl-dimethylsilyl)-oxy)], 25-trihydroxy-9,10-5(Z),7(E),10(19)-triene (132054-64-9)

Guidance literature:

(3-bromo-1,1-dimethylpropoxy)triethylsilane; 1α-[((trimethylsilyl)-oxy)]-3β-[((tertiarybutyl-dimethylsilyl)-oxy)]-20(S)-[[(p-tolylsulfonyl)oxy]methyl]-9,10-secopregna-5(Z),7(E),10(19)-triene; With copper(l) iodide; In tetrahydrofuran; diethyl ether; at 0 ℃; for 2h;

With potassium hydroxide; In ethanol; at 0 ℃; for 1h; Further stages.;

DOI:10.1021/ol0266931

upstream raw materials:

(3-bromo-1,1-dimethylpropoxy)triethylsilane

calcidiol

25-hydroxy-5E-[6,19,19'-H3]vitamin D3-3β-tert-butyldimethylsilyl ether

(R)-6-{(1R,3aS,7aR)-4-[1-[(S)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-1-yl]-meth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

Downstream raw materials:

1α,25-di-tetrahydropyranyloxy-3β-tert-butyldimethysilyl-5Z-vitamin D3

1α,25-di-tetrahydropyranyloxy-5Z-vitamin D3

C₃₉H₆₁BrO₆

1α,25-dihydroxycholecalciferol

Refernces

• 1、 Swann, Steve L.,Bergh, Joel J.,Farach-Carson, M. Cindy,Koh, John T.. "Rational Design of Vitamin D3 Analogues Which Selectively Restore Activity to a Vitamin D Receptor Mutant Associated with Rickets". . p. 3863 - 3866. Retrieved 2007/10/03.