1alpha,25-Dihydroxy-previtamin D3

Base Information

• Chemical Name: 1alpha,25-Dihydroxy-previtamin D3
• CAS No.: 57102-09-7
• Molecular Formula: C27H44 O3
• Molecular Weight: 416.645
• Metabolomics Workbench ID: 36200
• Mol file: 57102-09-7.mol

Synonyms:1 alpha,25-dihydroxy-previtamin D(3);1,25-dihydroxy-previtamin D(3);1,25-dihydroxy-previtamin D(3), (1alpha,3alpha,6Z)-isomer;1,25-dihydroxytachysterol

Chemical Property of 1alpha,25-Dihydroxy-previtamin D3

Chemical Property:

• Vapor Pressure: 4.28E-15mmHg at 25°C
• Boiling Point: 564.5°Cat760mmHg
• Flash Point: 238.2°C
• PSA: 60.69000
• Density: 1.119g/cm³
• LogP: 5.70470
• Storage Temp.: Amber Vial, -86°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 416.32904526
• Heavy Atom Count: 30
• Complexity: 701

Purity/Quality:

99% ^*data from raw suppliers

1,25-DihydroxyprevitaminD3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(CC(CC1O)O)C=CC2=CCCC3(C2CCC3C(C)CCCC(C)(C)O)C
• Isomeric SMILES: CC1=C(C[C@@H](C[C@H]1O)O)/C=C\C2=CCC[C@]3([C@H]2CC[C@@H]3[C@H](C)CCCC(C)(C)O)C
• Uses: 1α,25-Dihydroxyprevitamin D3 is used to stimulate expression and translocation of protein kinase Calpha and Cdelta via. It is related to Vitamin D (V676045)

Technology Process of 1alpha,25-Dihydroxy-previtamin D3

There total 25 articles about 1alpha,25-Dihydroxy-previtamin D3 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:

(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) → calcitriol (32222-06-3) + [2H]-Pre-1,25-D3 (57102-09-7)

Guidance literature:

With potassium hydroxide; In methanol; water; at 85 ℃; for 70h;

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

Reference yield:

1-Oxo-25-hydroxyprevitamin D3 (66760-28-9) → calcitriol (32222-06-3) + [2H]-Pre-1,25-D3 (57102-09-7)

Guidance literature:

With sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1021/jo00059a048

Reference yield:

de-A,B-25-cholesta-8,25-dien-8-yl trifluromethanesulfonate (113490-28-1) → [2H]-Pre-1,25-D3 (57102-09-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) mercuric acetate, 2.) aq. NaOH, NaBH₄ / 1.) THF, H₂O, RT, 1 h, 2.) THF, H₂O, RT, 30 min

2: 84 percent / diethylamine, CuI, bispalladium(II) acetate / dimethylformamide / 1.5 h / Ambient temperature

3: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 21 h / Ambient temperature

4: 90 percent / H₂, quinoline / Lindlar catalyst / methanol; hexane / 0.33 h

With quinoline; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; bispalladium(II) acetate; mercury(II) diacetate; tetrabutyl ammonium fluoride; hydrogen; diethylamine; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide;

DOI:10.1021/ja00018a038

upstream raw materials:

calcitriol

(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

1-Oxo-25-hydroxyprevitamin D₃

1α,3β,25-trihydroxycholesta-5,7-diene

Downstream raw materials:

1α,3β,25-trihydroxycholesta-5,7-diene

1a,25-Dihydroxytachysterol₃

calcitriol

Refernces

• 1、 Reichenbaecher,Gliesing,Lange,Gonschior,Schoenecker. "An effective procedure for the synthesis of 1α,25-dihydroxy-cholecalciferol (calcitriol) starting with 1α,3β, 25-trihydroxy-cholesta-5,7-diene (pro-calcitriol)". . p. 634 - 641. Retrieved 2007/10/03.
• 2、 Muralidharan, K. Raman,Lera, Angel R. de,Isaeff, Shawn D.,Norman, Anthony W.,Okamura, William H.. "Studies on the A-Ring Diastereomers of 1α,25-Dihydroxyvitamin D3". . p. 1895 - 1899. Retrieved 2007/10/02.