(1R)-25-Hydroxy-1-(hydroxymethyl)vitamin D3/(1R)-25-hydroxy-1-(hydroxymethyl)cholecalciferol

Base Information

• Chemical Name: (1R)-25-Hydroxy-1-(hydroxymethyl)vitamin D3/(1R)-25-hydroxy-1-(hydroxymethyl)cholecalciferol
• CAS No.: 142508-68-7
• Molecular Formula: C28H46 O3
• Molecular Weight: 430.671
• Metabolomics Workbench ID: 35886
• Mol file: 142508-68-7.mol

Synonyms:1-HBDV D3;1-hydroxymethyl-3-norhydroxy-3,25-dihydroxyvitamin D3

Chemical Property of (1R)-25-Hydroxy-1-(hydroxymethyl)vitamin D3/(1R)-25-hydroxy-1-(hydroxymethyl)cholecalciferol

Chemical Property:

• Vapor Pressure: 1.29E-15mmHg at 25°C
• Boiling Point: 575°Cat760mmHg
• Flash Point: 240.2°C
• PSA: 60.69000
• Density: 1.05g/cm³
• LogP: 5.95230
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 430.34469533
• Heavy Atom Count: 31
• Complexity: 703

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCCC(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)CO)O)C
• Isomeric SMILES: C[C@H](CCCC(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)CO)O)C

Technology Process of (1R)-25-Hydroxy-1-(hydroxymethyl)vitamin D3/(1R)-25-hydroxy-1-(hydroxymethyl)cholecalciferol

There total 6 articles about (1R)-25-Hydroxy-1-(hydroxymethyl)vitamin D3/(1R)-25-hydroxy-1-(hydroxymethyl)cholecalciferol 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: 76.0%

(1R,3aS,7aR)-4-[2-[(3R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((R)-1,5-dimethyl-5-trimethylsilanyloxy-hexyl)-7a-methyl-octahydro-indene → 1β-(hydroxymethyl)-3β-norhydroxy-3α,25-dihydroxyvitamin D3 (142508-68-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 14h;

DOI:10.1021/jm00095a026

Reference yield:

[(4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-1-enyl]-methanol (142508-73-4) → 1β-(hydroxymethyl)-3β-norhydroxy-3α,25-dihydroxyvitamin D3 (142508-68-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 2,4,6-trimethylbenzoic acid / CH₂Cl₂ / 12.5 h / 135 - 145 °C

2: DIBAL-H / toluene; hexane / 2 h / 0 °C

3: NCS, Me₂S / 1.08 h / -20 - 25 °C

4: 2.) 30percent aq. H₂O₂ / 1.) THF, 2.) CH₂Cl₂, 10 min

5: PhLi / tetrahydrofuran; diethyl ether / -78 - -65 °C

6: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 14 h / 25 °C

With N-chloro-succinimide; dimethylsulfide; mesitylenecarboxylic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; diisobutylaluminium hydride; phenyllithium; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;

DOI:10.1021/jm00095a026

Reference yield:

2-[(3R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-methylene-cyclohex-(E)-ylidene]-ethanol (142508-75-6) → 1β-(hydroxymethyl)-3β-norhydroxy-3α,25-dihydroxyvitamin D3 (142508-68-7)

Guidance literature:

Multi-step reaction with 4 steps

1: NCS, Me₂S / 1.08 h / -20 - 25 °C

2: 2.) 30percent aq. H₂O₂ / 1.) THF, 2.) CH₂Cl₂, 10 min

3: PhLi / tetrahydrofuran; diethyl ether / -78 - -65 °C

4: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 14 h / 25 °C

With N-chloro-succinimide; dimethylsulfide; tetrabutyl ammonium fluoride; dihydrogen peroxide; phenyllithium; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jm00095a026

upstream raw materials:

[(4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-1-enyl]-methanol

2-[(3R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-methylene-cyclohex-(E)-ylidene]-ethanol

(1R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-[2-chloro-eth-(E)-ylidene]-2-methylene-cyclohexane

[(3R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-methylene-cyclohex-(E)-ylidene]-acetic acid ethyl ester

Refernces