24R-Calcipotriol

Base Information

• Chemical Name: 24R-Calcipotriol
• CAS No.: 112827-99-3
• Molecular Formula: C27H40O3
• Molecular Weight: 412.613
• European Community (EC) Number: 601-218-4,688-306-6
• UNII: TYF37XV46I
• Nikkaji Number: J2.670.857E
• Wikipedia: Calcipotriol
• Wikidata: Q27290482
• Metabolomics Workbench ID: 35656
• Mol file: 112827-99-3.mol

Synonyms:24R-Calcipotriol;112827-99-3;Calcipotriol, 24R-;24R-Calcipotriene;24-epi--Calcipotriol;Calcipotriol Impurity D;PRI 2202;PRI-2202;UNII-TYF37XV46I;TYF37XV46I;Calcipotriol, anhydrous impurity D [EP];Calcipotriol, anhydrous specified impurity D [EP];(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5R)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol;1,3-Cyclohexanediol, 5-((2E)-2-((1R,3aS,7aR)-1-((1R,2E,4R)-4-cyclopropyl-4-hydroxy-1-methyl-2-buten-1-yl)octahydro-7a-methyl-4H-inden-4-ylidene)ethylidene)-4-methylene-, (1S,3S,5Z)-;(24R)-Calcipotriene;(22E)-(24R)-1alpha,24-dihydroxy-26,27-cyclo-22,23-didehydrovitamin D3 / (22E)-(24R)-1alpha,24-dihydroxy-26,27-cyclo-22,23-didehydrocholecalciferol;(5Z,7E,22E)-(1S,3R,24R)-26,27-cyclo-9,10-seco-5,7,10(19),22-cholestatetraene-1,3,24-triol;(5Z,7E,22E,24R)-24-Cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1alpha,3beta,24-triol;9,10-Secochola-5,7,10(19),22-tetraene-1,3,24-triol, 24-cyclopropyl-, (1alpha,3beta,5Z,7E,22E,24R)-;112965-21-6;SCHEMBL3278752;LMST03020105;AKOS040732272;CS-1164;HY-15266;CALCIPOTRIOL IMPURITY D [EP IMPURITY];CALCIPOTRIENE IMPURITY D [USP IMPURITY];Q27290482;CALCIPOTRIOL MONOHYDRATE IMPURITY D [EP IMPURITY];(5Z,7E,22E,24R)-24-CYCLOPROPYL-9,10-SECOCHOLA-5,7,10(19),22-TETRAENE-1.ALPHA.,3.BETA.,24-TRIOL;9,10-SECOCHOLA-5,7,10(19),22-TETRAENE-1,3,24-TRIOL, 24-CYCLOPROPYL-, (1.ALPHA.,3.BETA.,5Z,7E,22E,24R)-

Chemical Property of 24R-Calcipotriol

Chemical Property:

• Boiling Point: 582.0±50.0 °C(Predicted)
• PKA: 14.29±0.20(Predicted)
• PSA: 60.69000
• Density: 1.12±0.1 g/cm3(Predicted)
• LogP: 5.09060
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 412.29774513
• Heavy Atom Count: 30
• Complexity: 743

Purity/Quality:

99.90% ^*data from raw suppliers

(24R)-Calcipotriene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C=CC(C1CC1)O)C2CCC3C2(CCCC3=CC=C4CC(CC(C4=C)O)O)C
• Isomeric SMILES: C[C@H](/C=C/[C@@H](C1CC1)O)[C@H]2CC[C@@H]\3[C@@]2(CCC/C3=C\C=C/4\C[C@H](C[C@@H](C4=C)O)O)C
• Recent EU Clinical Trials: Exploratory study of the efficacy and safety of topical bimiralisib in an inflammatory and hyperproliferative skin condition
• Uses: (24R)-Calcipotriene is a synthetic analogs of vitamin D that was studied for its potential antitumor effects. Studies has shown the combined treatment with vitamin D analog (24R)-Calcipotriene was more effective than the treatment with cytostatics applied alone. (24R)-Calcipotriene is also the 24-R epimer of Calcipotriene (C144200).

Technology Process of 24R-Calcipotriol

There total 17 articles about 24R-Calcipotriol 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: 72.0%

(1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(R)-cycloprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10(19)-triene (112910-41-5,134523-61-8,910133-69-6,910133-34-5) → 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 (112827-99-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 60 ℃; for 0.833333h;

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

Reference yield:

(5Z,7E,22E)-(1S,3R,24R)-24-acetoxy-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol → 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 (112827-99-3) + calcipotriene (112965-21-6)

Guidance literature:

With silica gel; In hexane; dichloromethane; for 24h; Product distribution / selectivity;

Reference yield:

Cyclopropyl methyl ketone (765-43-5) → 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 (112827-99-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 87 percent / bromine / methanol / 0.5 h / Ambient temperature

2: 84 percent

3: 86 percent / 2N sodium hydroxide / H₂O; CH₂Cl₂

5: N-methylmorpholine N-oxide, selenium dioxide

6: imidazole / dimethylformamide

7: 55 percent / NaBH₄, CeCl₃*6H₂O / methanol / further reag.: (S)-BINAL-H

8: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation

9: 72 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; selenium(IV) oxide; cerium(III) chloride; anthracene; tetrabutyl ammonium fluoride; bromine; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

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

upstream 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

Cyclopropyl methyl ketone

2-bromo-1-cyclopropylethan-1-one

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

Refernces

• 1、 Calverley. "Synthesis of MC 903, a biologically active vitamin D metabolite analogue". . p. 4609 - 4619,4609-4619. Retrieved 2007/10/02.