1,25-dihydroxyvitamin D3-26,23-lactone

Base Information

• Chemical Name: 1,25-dihydroxyvitamin D3-26,23-lactone
• CAS No.: 81203-50-1
• Molecular Formula: C₂₇H₄₀O₅
• Molecular Weight: 444.612
• DSSTox Substance ID: DTXSID1051359
• Wikidata: Q27075646
• Pharos Ligand ID: ZB992AUC7BPY
• Metabolomics Workbench ID: 35674
• Mol file: 81203-50-1.mol

Synonyms:1 alpha,25-dihydroxyvitamin D3-26,23-lactone;1,25-dihydroxycholecalciferol-26-23-lactone;1,25-dihydroxyvitamin D3-26,23-lactone;1,25-lactone;23(S),25(R)-1,25(OH)2D3-26,23-lactone;calcitriol-26,23-lactone

Chemical Property of 1,25-dihydroxyvitamin D3-26,23-lactone

Chemical Property:

• Vapor Pressure: 3.41E-18mmHg at 25°C
• Boiling Point: 624.1°C at 760 mmHg
• PKA: 13.13±0.40(Predicted)
• Flash Point: 204.8°C
• PSA: 86.99000
• Density: 1.18g/cm³
• LogP: 4.22010
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 444.28757437
• Heavy Atom Count: 32
• Complexity: 828

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

CalcitriolLactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC1CC(C(=O)O1)(C)O)C2CCC3C2(CCCC3=CC=C4CC(CC(C4=C)O)O)C
• Isomeric SMILES: C[C@H](C[C@H]1C[C@@](C(=O)O1)(C)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
• Uses: Calcitriol Lactone is a metabolite of Calcitriol (C144500), which is an active form of Vitamin D3. Calcitriol is also a calcium regulator.

Technology Process of 1,25-dihydroxyvitamin D3-26,23-lactone

There total 21 articles about 1,25-dihydroxyvitamin D3-26,23-lactone 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: 68.0%

(3R,5S)-5-((R)-2-((1R,3αR,7αR,E)-4-(bromomethylene)-7α-methyloctahydro-1H-inden-1-yl)propyl)-3-methyl-3-((triethylsilyl)-oxy)dihydrofuran-2(3H)-one + (3S,5R)-3,5-bis(t-butyldimethylsilyloxy)octa-1-en-7-yne (161055-41-0) → (3R,5S)-5-((R)-2-((1R,3αS,7αR,E)-4-((Z)-2-((3S,5R)-3,5-dihydroxy-2-methylenecyclohexylidene)ethylidene)-7α-methyloctahydro-1H-inden-1-yl)propyl)-3-hydroxy-3-methyldihydrofuran-2(3H)-one (81203-50-1,75519-08-3,87680-15-7,90320-03-9,90320-04-0,95464-24-7,95464-25-8)

Guidance literature:

(3R,5S)-5-((R)-2-((1R,3αR,7αR,E)-4-(bromomethylene)-7α-methyloctahydro-1H-inden-1-yl)propyl)-3-methyl-3-((triethylsilyl)-oxy)dihydrofuran-2(3H)-one; (3S,5R)-3,5-bis(t-butyldimethylsilyloxy)octa-1-en-7-yne; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In toluene; at 90 ℃; for 1h;

With triethylamine tris(hydrogen fluoride); In tetrahydrofuran; at 0 ℃; for 48h;

DOI:10.1021/acs.joc.9b00403

Reference yield: 39.0%

previtamin D3 → (3R,5S)-5-((R)-2-((1R,3αS,7αR,E)-4-((Z)-2-((3S,5R)-3,5-dihydroxy-2-methylenecyclohexylidene)ethylidene)-7α-methyloctahydro-1H-inden-1-yl)propyl)-3-hydroxy-3-methyldihydrofuran-2(3H)-one (81203-50-1,75519-08-3,87680-15-7,90320-03-9,90320-04-0,95464-24-7,95464-25-8)

Guidance literature:

In ethanol; 1.) reflux, 45 min, 2.) 5 deg C, 10 d;

DOI:10.1021/jo00027a010

Reference yield:

Acetic acid (3aR,4R,7aS)-1-eth-(Z)-ylidene-7a-methyl-octahydro-inden-4-yl ester (81506-36-7) → (3R,5S)-5-((R)-2-((1R,3αS,7αR,E)-4-((Z)-2-((3S,5R)-3,5-dihydroxy-2-methylenecyclohexylidene)ethylidene)-7α-methyloctahydro-1H-inden-1-yl)propyl)-3-hydroxy-3-methyldihydrofuran-2(3H)-one (81203-50-1,75519-08-3,87680-15-7,90320-03-9,90320-04-0,95464-24-7,95464-25-8)

Guidance literature:

Multi-step reaction with 10 steps

1: ethylaluminum dichloride / CH₂Cl₂ / 25 h / 0 deg C to room temp.

2: 91 percent / diisobutylaluminum hydride / tetrahydrofuran / 0 deg C to room temp.

3: 84 percent / KO-t-Bu / 2-methyl-propan-2-ol / Ambient temperature

4: 72 percent / H₂ / 5percent Pt on C / ethyl acetate

5: 99 percent / ethyl acetate / Ambient temperature

6: tetrahydrofuran / -78 deg C to room temp.

7: 2,2'-bipyridinium chlorochromate / CH₂Cl₂

9: 90 percent / tetrahydrofuran / -78 °C

10: ion exchange resin AG 50W-X₄, 200-400 mesh, H⁺-form, Bio-Rad Laboratories / methanol

With 200-400 mesh; Bio-Rad Laboratories; ion exchange resin AG 50W-X₄; potassium tert-butylate; hydrogen; ethylaluminum dichloride; hydrogen cation; diisobutylaluminium hydride; 2,2'-bipyridinium chlorochromate; platinum on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; tert-butyl alcohol;

DOI:10.1021/jo00171a068

upstream raw materials:

(3R,5S)-5-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-3-methyl-3-trimethylsilanyloxy-dihydro-furan-2-one

(23S,25R)-1α,3β,25-trihydroxy-5,7-cholestadiene 26,23-lactone

(23S,25R)-1α,3β,25-trihydroxy-5,7-cholestadiene 26,23-lactone 4-phenyl-1,2,4-triazoline-3,5-dione adduct

(22S,23R,25R)-1α,3β,25-trihydroxy-22-iodo-5,7-cholestadiene 26,23-lactone 4-phenyl-1,2,4-triazoline-3,5-dione adduct