(1R,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

Base Information

• Chemical Name: (1R,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
• CAS No.: 32511-63-0
• Deprecated CAS: 31448-33-6
• Molecular Formula: C27H44O3
• Molecular Weight: 416.645
• DSSTox Substance ID: DTXSID80873390
• Mol file: 32511-63-0.mol

Synonyms:1 alpha, 25-dihydroxy-20-epi-Vitamin D3;1 alpha,25 Dihydroxyvitamin D3;1 alpha,25-Dihydroxycholecalciferol;1 alpha,25-Dihydroxyvitamin D3;1, 25-(OH)2D3;1,25 dihydroxy 20 epi Vitamin D3;1,25 Dihydroxycholecalciferol;1,25 Dihydroxyvitamin D3;1,25(OH)2-20epi-D3;1,25(OH)2D3;1,25-dihydroxy-20-epi-Vitamin D3;1,25-Dihydroxycholecalciferol;1,25-Dihydroxyvitamin D3;20-epi-1alpha,25-dihydroxycholecaliferol;Bocatriol;Calcijex;Calcitriol;Calcitriol KyraMed;Calcitriol Nefro;Calcitriol-Nefro;D3, 1 alpha,25-Dihydroxyvitamin;D3, 1,25-dihydroxy-20-epi-Vitamin;D3, 1,25-Dihydroxyvitamin;Decostriol;KyraMed, Calcitriol;MC 1288;MC-1288;MC1288;Osteotriol;Renatriol;Rocaltrol;Silkis;Sitriol;Soltriol;Tirocal

Chemical Property of (1R,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

Chemical Property:

• Vapor Pressure: 4.05E-15mmHg at 25°C
• Boiling Point: 565°Cat760mmHg
• PKA: 14.43±0.40(Predicted)
• Flash Point: 238.4°C
• PSA: 60.69000
• Density: 1.06g/cm³
• LogP: 5.70470
• 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

1,25-Dihydroxyvitamin D3 ^*data from reagent suppliers

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)O)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](CC(C3=C)O)O)C

Technology Process of (1R,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

There total 13 articles about (1R,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol 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:

vitamin D3 (67-97-0) → calcidiol (19356-17-3) + calcitriol (32511-63-0)

Guidance literature:

With water; at 28 ℃; for 48h; Reagent/catalyst; Microbiological reaction;

DOI:10.1002/cbic.202100027

Reference yield:

(1S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[2-[(1R,3aS)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-2-methylene-cyclohexanol (132054-64-9) → 1α,25-dihydroxycholecalciferol (32222-06-3,32511-63-0,61476-45-7,66791-71-7,73837-24-8,75917-61-2,96614-28-7,96646-17-2,134523-84-5,142864-52-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Yield given;

DOI:10.1021/jo00359a061

Reference yield:

(S)-3-[(R)-1-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ6-benzo[c]thiophen-5-ol (73809-11-7,73824-80-3,87237-31-8,87237-32-9) → 1α,25-dihydroxycholecalciferol (32222-06-3,32511-63-0,61476-45-7,66791-71-7,73837-24-8,75917-61-2,96614-28-7,96646-17-2,134523-84-5,142864-52-6)

Guidance literature:

Multi-step reaction with 5 steps

1: NaHCO₃ / ethanol / Heating

2: imidazole / dimethylformamide

3: SeO₂, N-methylmorpholine N-oxide / methanol; CH₂Cl₂ / Heating

4: acridine / Irradiation

5: (C₄H₉)4N¹⁺*F^1- / tetrahydrofuran

With 1H-imidazole; acridine; selenium(IV) oxide; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00359a061

upstream raw materials:

vitamin D₃

(1S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[2-[(1R,3aS)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-2-methylene-cyclohexanol

(S)-3-[(R)-1-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-5-ol

(R)-6-{(1R,3aS)-4-[2-[(S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

Refernces

• 1、 Andrews,Barton,Cheng,et al.. "A direct, regio- and stereoselective 1α-hydroxylation of (5E)-calciferol derivatives". . p. 1635 - 1637. Retrieved 2007/10/02.