1H,5H-Cyclopenta[f][1,2,4]triazolo[1,2-a]cinnoline-1,3(2H)-dione, 11-(3,5-dihydroxy-2-methyl-1-cyclohexen-1-yl)-4a,6,6a,7,8,9,9a,11-octa hydro-7-(5-hydroxy-1,5-dimethylhexyl)-6a-methyl-2-phenyl-, [4aR-[4aa,6aa,7a(R*),9ab,11a(3S*,5R*)]]-

Base Information

• Chemical Name: 1H,5H-Cyclopenta[f][1,2,4]triazolo[1,2-a]cinnoline-1,3(2H)-dione, 11-(3,5-dihydroxy-2-methyl-1-cyclohexen-1-yl)-4a,6,6a,7,8,9,9a,11-octa hydro-7-(5-hydroxy-1,5-dimethylhexyl)-6a-methyl-2-phenyl-, [4aR-[4aa,6aa,7a(R*),9ab,11a(3S*,5R*)]]-
• CAS No.: 86307-44-0
• Molecular Formula: C35H49N3O5
• Molecular Weight: 591.791
• Mol file: 86307-44-0.mol

Synonyms:pre-Calcitriol PTAD Adduct;[4aR-[4aα,6aα,7α(R*),9aβ,11α(3S*,5R*)]]-11-(3,5-Dihydroxy-2-Methyl-1-cyclohexen-1-yl)-4a,6,6a,7,8,9,9a,11-octahydro-7-(5-hydroxy-1,5-diMethylhexyl)-6a-Methyl-2-phenyl-1H,5H-cyclopenta[f][1,2,4]triazolo[1,2-a]cinnoline-1,3(2H)-di;(6aR,7R,9aR)-11-((3S,5R)-3,5-dihydroxy-2-Methylcyclohex-1-en-1-yl)-7-((R)-6-hydroxy-6-Methylheptan-2-yl)-6a-Methyl-2-phenyl-4a,5,6,6a,7,8,9,9a-octahydrocyclopenta[f][1,2,4]triazolo[1,2-a]cinnoline-1,3(2H,11H)-dione;1H,5H-Cyclopenta[f][1,2,4]triazolo[1,2-a]cinnoline-1,3(2H)-dione, 11-(3,5-dihydroxy-2-Methyl-1-cyclohexen-1-yl)-4a,6,6a,7,8,9,9a,11-octahydro-7-(5-hydroxy-1,5-diMethylhexyl)-6a-Methyl-2-phenyl-, [4aR-[4aα,6aα,7α(R*),9aβ,11α(3S*,5R;IMpurity C of Calcitriol

Chemical Property of 1H,5H-Cyclopenta[f][1,2,4]triazolo[1,2-a]cinnoline-1,3(2H)-dione, 11-(3,5-dihydroxy-2-methyl-1-cyclohexen-1-yl)-4a,6,6a,7,8,9,9a,11-octa hydro-7-(5-hydroxy-1,5-dimethylhexyl)-6a-methyl-2-phenyl-, [4aR-[4aa,6aa,7a(R*),9ab,11a(3S*,5R*)]]-

Chemical Property:

• Boiling Point: 707.5±70.0 °C(Predicted)
• PSA: 109.62000
• Density: 1.27±0.1 g/cm3(Predicted)
• LogP: 5.05860

Purity/Quality:

98% ^*data from raw suppliers

pre-CalcitriolPTADAdduct(MixtureofDiastereomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Calcitriol (C144500) impurity. 1α-Hydroxyvitamin D and 1α-hydroxyprevitamin D compounds were prepared in multistep syntheses via hydroxylation of previtamin D compound adducts with dienophiles.

Technology Process of 1H,5H-Cyclopenta[f][1,2,4]triazolo[1,2-a]cinnoline-1,3(2H)-dione, 11-(3,5-dihydroxy-2-methyl-1-cyclohexen-1-yl)-4a,6,6a,7,8,9,9a,11-octa hydro-7-(5-hydroxy-1,5-dimethylhexyl)-6a-methyl-2-phenyl-, [4aR-[4aa,6aa,7a(R*),9ab,11a(3S*,5R*)]]-

There total 6 articles about 1H,5H-Cyclopenta[f][1,2,4]triazolo[1,2-a]cinnoline-1,3(2H)-dione, 11-(3,5-dihydroxy-2-methyl-1-cyclohexen-1-yl)-4a,6,6a,7,8,9,9a,11-octa hydro-7-(5-hydroxy-1,5-dimethylhexyl)-6a-methyl-2-phenyl-, [4aR-[4aa,6aa,7a(R*),9ab,11a(3S*,5R*)]]- 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: 73.0%

(3bR,5aR,6R,8aR,10S)-6-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-10-((R)-5-hydroxy-2-methyl-3-oxo-cyclohex-1-enyl)-5a-methyl-2-phenyl-4,5,5a,6,7,8,8a,10-octahydro-3bH-2,3a,10a-triaza-dicyclopenta[a,f]naphthalene-1,3-dione (86307-43-9) → (3bR,5aR,6R,8aR,10S)-10-((3S,5R)-3,5-Dihydroxy-2-methyl-cyclohex-1-enyl)-6-((R)-5-hydroxy-1,5-dimethyl-hexyl)-5a-methyl-2-phenyl-4,5,5a,6,7,8,8a,10-octahydro-3bH-2,3a,10a-triaza-dicyclopenta[a,f]naphthalene-1,3-dione (86307-44-0)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride; In tetrahydrofuran; at -60 ℃; for 1h;

DOI:10.1016/S0040-4020(01)83478-5

Reference yield:

4-Phenylurazole (15988-11-1) → (3bR,5aR,6R,8aR,10S)-10-((3S,5R)-3,5-Dihydroxy-2-methyl-cyclohex-1-enyl)-6-((R)-5-hydroxy-1,5-dimethyl-hexyl)-5a-methyl-2-phenyl-4,5,5a,6,7,8,8a,10-octahydro-3bH-2,3a,10a-triaza-dicyclopenta[a,f]naphthalene-1,3-dione (86307-44-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 49 percent / CH₂Cl₂ / 10 °C

2: 92 percent / imidazole / dimethylformamide / 5 h / 25 °C

3: 1.) 1,3-dibromo-5,5-dimethyl hydantoin, collidine, AIBN; 2.) bis-tetrabutylammoniumdichromate / 1.) hexane, CH₂Cl₂, reflux, 20 min; 2.) CHCl₃, reflux, 3 h

4: 84 percent / n-butyric acid, tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

5: 73 percent / LiAlH₄, AlCl₃ / tetrahydrofuran / 1 h / -60 °C

With 1H-imidazole; 2,3,5-trimethyl-pyridine; lithium aluminium tetrahydride; aluminium trichloride; tetra(n-butyl)ammonium dichromate(VI); 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; butyric acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)83478-5

Reference yield:

25-hydroxy previtamin D3 (23357-18-8) → (3bR,5aR,6R,8aR,10S)-10-((3S,5R)-3,5-Dihydroxy-2-methyl-cyclohex-1-enyl)-6-((R)-5-hydroxy-1,5-dimethyl-hexyl)-5a-methyl-2-phenyl-4,5,5a,6,7,8,8a,10-octahydro-3bH-2,3a,10a-triaza-dicyclopenta[a,f]naphthalene-1,3-dione (86307-44-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 49 percent / CH₂Cl₂ / 10 °C

2: 92 percent / imidazole / dimethylformamide / 5 h / 25 °C

3: 1.) 1,3-dibromo-5,5-dimethyl hydantoin, collidine, AIBN; 2.) bis-tetrabutylammoniumdichromate / 1.) hexane, CH₂Cl₂, reflux, 20 min; 2.) CHCl₃, reflux, 3 h

4: 84 percent / n-butyric acid, tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

5: 73 percent / LiAlH₄, AlCl₃ / tetrahydrofuran / 1 h / -60 °C

With 1H-imidazole; 2,3,5-trimethyl-pyridine; lithium aluminium tetrahydride; aluminium trichloride; tetra(n-butyl)ammonium dichromate(VI); 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; butyric acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)83478-5

upstream raw materials:

(3bR,5aR,6R,8aR,10S)-6-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-10-((R)-5-hydroxy-2-methyl-3-oxo-cyclohex-1-enyl)-5a-methyl-2-phenyl-4,5,5a,6,7,8,8a,10-octahydro-3bH-2,3a,10a-triaza-dicyclopenta[a,f]naphthalene-1,3-dione

4-Phenylurazole

25-hydroxy previtamin D₃

(3bR,5aR,6R,8aR,10S)-6-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-10-((S)-5-hydroxy-2-methyl-cyclohex-1-enyl)-5a-methyl-2-phenyl-4,5,5a,6,7,8,8a,10-octahydro-3bH-2,3a,10a-triaza-dicyclopenta[a,f]naphthalene-1,3-dione

Downstream raw materials:

calcitriol

[2H]-Pre-1,25-D₃

Refernces