1alpha,25-Dihydroxyvitamin D3

Base Information

• Chemical Name: 1alpha,25-Dihydroxyvitamin D3
• CAS No.: 32222-06-3
• Molecular Formula: C27H44O3
• Molecular Weight: 416.645
• Hs Code.: 29061900
• Mol file: 32222-06-3.mol

Synonyms:Toptriol;Dihydroxyvitamin D3;DN 101;1.alpha.,25-dihydroxycholecalciferol;9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol, (1.alpha.,3.beta.,5Z,7E)-;GMRQFYUYWCNGIN-CLVAPQHMSA-N;1.alpha.,25-Dihydroxyvitamin D3;AKOS025401842;Cholecalciferol, 1.alpha.,25-dihydroxy-;(3.beta.,5Z,7E)-9,10-Secocholesta-5,7,10-triene-1,3,25-triol;(5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-1.alpha.,3.beta.,25-triol

Chemical Property of 1alpha,25-Dihydroxyvitamin D3

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 119-121 °C
• Refractive Index: 1.547
• Boiling Point: 565 °C at 760 mmHg
• PKA: 14.43±0.40(Predicted)
• Flash Point: 238.4 °C
• PSA: 60.69000
• Density: 1.06 g/cm³
• LogP: 5.70470
• Storage Temp.: 2-8°C
• Solubility.: Do you have solubility information on this product that you woul
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 416.32904526
• Heavy Atom Count: 30
• Complexity: 688

Purity/Quality:

99%, ^*data from raw suppliers

Calcitriol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,Xn
• Hazard Codes: T+,Xn,F
• Statements: 26/27/28-63-36/37/38-20/21/22-11
• Safety Statements: 36/37/39-45-36-26-16-7

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCCC(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C
• Isomeric SMILES: CC(CCCC(C)(C)O)C1CCC\2C1(CCC/C2=C\C=C\3/CC(CC(C3=C)O)O)C
• General Description: Calcitriol, also known as 1α,25-dihydroxyvitamin D₃ or 1,25-(OH)₂D₃, is the biologically active form of vitamin D₃. It plays a critical role in calcium homeostasis, bone metabolism, and cell differentiation by binding to the vitamin D receptor (VDR). Research has explored its synthesis and structural analogues, aiming to enhance VDR binding affinity or dissociate therapeutic effects (e.g., antiproliferative activity) from calcemic side effects. Key synthetic strategies include enantioselective A-ring intermediate preparation and D-ring modifications, yielding analogues with potential clinical applications.

Technology Process of 1alpha,25-Dihydroxyvitamin D3

There total 255 articles about 1alpha,25-Dihydroxyvitamin 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: 100.0%

C30H52O3Si → calcitriol (32222-06-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 10h; Inert atmosphere;

DOI:10.1039/c2ob25511a

Reference yield: 95.0%

C45H86O3Si3 → 2-methylene-19-nor-(20S)-1α,25-dihydroxyvitamin D3 + 1α,25-dihydroxy-2-methylene-19-nor-vitamin D3 + calcitriol (32222-06-3)

Guidance literature:

With AG 50W-X₄ resin; In methanol; benzene; at 20 ℃; for 19h;

Reference yield: 95.0%

(1R,3aS,7aR)-1-((R)-5-Methoxymethoxy-1,5-dimethyl-hexyl)-7a-methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-indene (873567-12-5) → calcitriol (32222-06-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/ol052489c

upstream raw materials:

(1R,3aR,7aR)-1-{(1R)-1,5-dimethyl-5-[(trimethylsilyl)oxy]hexyl}-7a-methyloctahydro-4H-inden-4-one

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

methyllithium

1α-Hydroxy-25-oxo-27-norvitamin D₃

Downstream raw materials:

(1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol

(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

24,25,26,27-tetranor-1,23-(OH)2D₃

1α,25-dihydroxy-24-oxo-vitamin D3

Refernces

Enantioselective synthesis of a key A-ring intermediate for the preparation of 1α,25-dihydroxyvitamin D₃

10.1021/ol102586w

The research focuses on the enantioselective synthesis of a key A-ring intermediate, specifically the R,β-unsaturated aldehyde 1, which is crucial for the preparation of 1α,25-dihydroxyvitamin D3 (calcitriol). The purpose of this study is to develop a novel and efficient approach to synthesize this intermediate, starting from the inexpensive material (R)-carvone, with the potential to create vitamin D3 analogues with modifications at the C-2 position. The research concludes that a new strategy has been successfully developed, which involves 11 steps and yields the desired intermediate in 24% overall yield, with the ene reaction as the key step. This method could be applied to synthesize vitamin D3 analogues with modifications at the C-2 position, which may have increased binding affinity for the vitamin D receptor (VDR) and potent agonistic activity. Key chemicals used in the process include (R)-carvone, LAH, m-CPBA, nitrobenzoate, MOM group, Zn powder, NaI, and active forms of formaldehyde, among others.

Vitamin D₃: Synthesis of seco-C-9,11-bisnor-17-methyl-1α,25-dihydroxyvitamin D₃ analogues

10.1016/S0960-894X(02)00222-6

The study investigates the synthesis and biological properties of novel D-ring analogues of 1a,25-dihydroxyvitamin D3 (calcitriol). The researchers aimed to develop analogues that can dissociate cell-differentiating effects from calcemic effects, focusing on 17-methyl D-ring analogues lacking the six-membered C-ring. The synthesis involved the Lythgoe coupling of an 8-formyl-D-ring fragment with phosphine oxides, leading to the creation of analogues with both natural (R) and unnatural (S) configurations at C-20. The study evaluated the affinity of these analogues to the vitamin D receptor (VDR) and their antiproliferative activities in various cell lines, finding that some analogues, particularly the hexafluoro analogues, displayed high antiproliferative activity and significant differentiation between antiproliferative and calcemic effects. The chemicals involved included 1a,25-dihydroxyvitamin D3, various phosphine oxides, and a series of ketones used in the synthesis process.

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