1-Hydroxyprevitamin D3

Base Information

• Chemical Name: 1-Hydroxyprevitamin D3
• CAS No.: 41461-13-6
• Molecular Formula: C27H44 O2
• Molecular Weight: 400.645
• Wikidata: Q76389791
• Metabolomics Workbench ID: 36197
• Mol file: 41461-13-6.mol

Synonyms:1 alpha-hydroxyprevitamin D3;1-hydroxyprevitamin D3;1-hydroxyprevitamin D3, (1beta,3beta,6Z)-isomer;oxydevit;pre-1 alpha-hydroxyvitamin D3

Chemical Property of 1-Hydroxyprevitamin D3

Chemical Property:

• Vapor Pressure: 1.7E-13mmHg at 25°C
• Boiling Point: 531.1°Cat760mmHg
• Flash Point: 222.4°C
• PSA: 40.46000
• Density: 1.068g/cm³
• LogP: 6.58980
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 400.334130642
• Heavy Atom Count: 29
• Complexity: 655

Purity/Quality:

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)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)C

Technology Process of 1-Hydroxyprevitamin D3

There total 11 articles about 1-Hydroxyprevitamin 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)-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 (82266-85-1) → 1α-hydroxyprecalciferol3 (41461-13-6)

Guidance literature:

With potassium hydroxide; In methanol; at 80 ℃; for 24h;

DOI:10.1016/S0040-4039(00)87003-3

Reference yield:

1α-hydroxyprecalciferol3 diacetate (51261-53-1,54712-17-3,67113-61-5) → 1α-hydroxyprecalciferol3 (41461-13-6)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 2h;

Reference yield:

1α,3β-diacetoxy-9,10-seco-cholesta-5(10),8-diene-6-yne (51192-81-5) → 1α-hydroxyprecalciferol3 (41461-13-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / H₂ / presaturated Lindlar palladium catalyst, poisoned with quinoline / light petroleum / 0.3 h / 17 °C

2: MeONa / methanol / 2 h / 20 °C

With hydrogen; sodium methylate; poisoned with quinoline; presaturated Lindlar palladium catalyst; In methanol; Petroleum ether;

upstream raw materials:

(3bR,5aR,6R,8aR,10S)-10-((3S,5R)-3,5-Dihydroxy-2-methyl-cyclohex-1-enyl)-6-((R)-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-keto previtamin D₃

1α-hydroxyprecalciferol₃ diacetate

(3bR,5aR,6R,8aR,10R)-10-((3S,5R)-3,5-Dihydroxy-2-methyl-cyclohex-1-enyl)-6-((R)-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

Downstream raw materials:

1α-hydroxyvitamin D3

Refernces

• 1、 Vanmaele, L. J.,Clercq, P. J. De,Vandewalle, M.,Halkes, S. J.,Overbeek, W. R. M.. "1α-HYDROXY PREVITAMIN D3 AND ITS SELECTIVE FORMATION FROM 1-KETO PREVITAMIN D3". . p. 1179 - 1182. Retrieved 2007/10/02.
• 2、 Lithgoe, Basil,Waterhouse, Ian. "Calciferol and its Relatives. Part 28. A Stereoselective Synthesis of 1α-Hydroxyprecalciferol3 from 8-Hydroxymethyl-des-AB-cholest-8-ene". . p. 1405 - 1406. Retrieved 2007/10/02.