Ercalcitriol

Base Information

• Chemical Name: Ercalcitriol
• CAS No.: 60133-18-8
• Molecular Formula: C28H44O3
• Molecular Weight: 428.656
• European Community (EC) Number: 634-659-6
• UNII: 5RWP08OQ36
• DSSTox Substance ID: DTXSID90429509
• Wikidata: Q27159080
• Metabolomics Workbench ID: 35524
• ChEMBL ID: CHEMBL4303615
• Mol file: 60133-18-8.mol

Synonyms:1 alpha,25-dihydroxyvitamin D2;1,25-(OH)2D2;1,25-dihydroxyergocalciferol;1,25-dihydroxyergocalciferol, (1alpha,3beta,5Z,7E,22E)-isomer;1,25-dihydroxyvitamin D2;PRI-1906

Chemical Property of Ercalcitriol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.554
• Boiling Point: 577.655 °C at 760 mmHg
• PKA: 14.43±0.40(Predicted)
• Flash Point: 242.511 °C
• PSA: 60.69000
• Density: 1.066 g/cm³
• LogP: 5.72670
• Storage Temp.: −20°C
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 428.32904526
• Heavy Atom Count: 31
• Complexity: 758

Purity/Quality:

99% ^*data from raw suppliers

1α,25-Dihydroxyvitamin D2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,T+,F
• Statements: 23/24/25-63-48/25-26-24/25-11
• Safety Statements: 36/37-45-28-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C=CC(C)C(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C
• Isomeric SMILES: C[C@H](/C=C/[C@H](C)C(C)(C)O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](C[C@@H](C3=C)O)O)C
• Uses: The active metabolite of Vitamin D2 (V676040). This product may be used as an analytical standard.

Technology Process of Ercalcitriol

There total 60 articles about Ercalcitriol 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: 82.0%

1α-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]previtamin D2 tert-butyldimethylsilyl ether (145354-39-8) → ercalcitriol (60133-18-8)

Guidance literature:

With ion-exchange resin AG 50W-X₄; In methanol; for 48h; Ambient temperature; in the dark;

DOI:10.1021/jo00053a024

Reference yield:

aqueous potassium nitrate + (22E)-5,7,22-ergostatriene-1α,3β,25-triol (125732-35-6) → ercalcitriol (60133-18-8)

Guidance literature:

In tetrahydrofuran; ethanol; nitrogen;

Reference yield:

Benzoic acid (1R,3aR,4S,7aR)-7a-methyl-1-((S)-1-methyl-2-oxo-ethyl)-octahydro-inden-4-yl ester (66774-71-8) → ercalcitriol (60133-18-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 1) 2,6-di-tert-butylpyridine, 2a) TMSTf, 2b) Et₃N, MeOH / 1) CH₂Cl₂, -78 deg C, 5 min, 2a) -78 deg C, 2 h, 2b) -78 deg C, 5 min then to RT

2: TiCl₄ / CH₂Cl₂ / 12 h / -78 °C

3: 92 percent / DMAP, i-Pr₂NEt / CH₂Cl₂ / 18 h / 0 °C

4: 91 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

6: 1) LDA / 1) -78 deg C

7: 94 percent / Et₃N / (Ph₃P)2PdCl₂ / 75 °C

8: H₂, Lindlar catalyst, quinoline / hexane

9: 2,2,4-trimethyl-pentane / Heating

10: 82 percent / ion-exchange resin AG 50W-X₄ / methanol / 48 h / Ambient temperature; in the dark

With quinoline; methanol; dmap; Lindlar's catalyst; 2,6-di-tert-butyl-pyridine; TMSTf; ion-exchange resin AG 50W-X₄; hydrogen; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; hexane; dichloromethane;

DOI:10.1021/jo00053a024

upstream raw materials:

1R-<1α(1R*,2E,4S*),3aβ,7aα>-octahydro-1-<5-<(trimethylsilyl)oxy>-1,4,5-trimethyl-2-hexenyl>-7a-methyl-4H-inden-4-one

[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

1α-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]previtamin D₂ tert-butyldimethylsilyl ether

previtamin D

Refernces

• 1、 Granja,Castedo,Mourino. "Studies on the opening of dioxanone and acetal templates and application to the synthesis of 1α,25-dihydroxyvitamin D2". . p. 124 - 131. Retrieved 2007/10/02.
• 2、 Tsuji,Yokoyama,Tachibana. "A new and convenient synthesis of 1α,25-dihydroxyvitamin D2 and its 24R-epimer". . p. 3132 - 3137. Retrieved 2007/10/02.