5,6-trans-Vitamin D2

Base Information

• Chemical Name: 5,6-trans-Vitamin D2
• CAS No.: 51744-66-2
• Molecular Formula: C28H44O
• Molecular Weight: 396.657
• European Community (EC) Number: 200-014-9
• UN Number: 2811
• UNII: LYM8W766XP
• Nikkaji Number: J3.429.168C
• Wikipedia: Ergocalciferol
• Wikidata: Q105162130
• Metabolomics Workbench ID: 35506
• Mol file: 51744-66-2.mol

Synonyms:5,6-trans-Vitamin D2;trans-Vitamin D2;5,6-trans-Ergocalcifero;51744-66-2;LYM8W766XP;50-14-6;Davitin;Metadee;Mykostin;Radiostol;(1S,3E)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol;Decaps;Infron;Shock-ferol;Davitamon D;Dee-Osterol;Dee-Roual;vitamin d-2;Buco-D;(5E,7E,22E)-(3S)-9,10-seco-5,7,10(19),22-ergostatetraen-3-ol;(5E)-vitamin D2 / 5,6-trans-vitamin D2 / (5E)-ergocalciferol / (5E)-ercalciol;DTXCID70233;Ergocalciferol;(Vitamin D2);Ergocalciferol [BAN:INN:JAN];Ergocalciferol [INN:BAN:JAN];C28-H44-O;CAS-50-14-6;NCGC00166307-01;UNII-LYM8W766XP;SCHEMBL1651665;Ergocalciferol impurity A [EP];(3-beta,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol;CHEBI:181420;Ciclohexanol, 4-metilen-3-[(2E)-2-[(1R, 3aS, 7aR)-octahidro-7a-metil-1-[(1R, 2E, 4R)-1,4,5-trimetil-2-hexen-1-il]-4H-inden-4-ilideno] etilideno]-, (1S, 3Z)-;Tox21_112404;Tox21_202348;Tox21_302752;HY-76542A;LMST03010014;AKOS026750022;CS-O-01458;NCGC00166307-05;NCGC00166307-06;NCGC00179579-01;NCGC00179579-02;NCGC00256529-01;NCGC00259897-01;MS-26694;PD167231;CS-0111409;E81381;ERGOCALCIFEROL IMPURITY A [EP IMPURITY];(3beta,5E,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol;(5E,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3beta-ol;(5E,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraene-3beta-ol;9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol, (3beta,5E,7E,22E)-;(5E,7E,22E)-9,10-SECOERGOSTA-5,7,10(19),22-TETRAEN-3.BETA.-OL;9,10-SECOERGOSTA-5,7,10(19),22-TETRAEN-3-OL, (3.BETA.,5E,7E,22E)-

Chemical Property of 5,6-trans-Vitamin D2

Chemical Property:

• PSA: 20.23000
• LogP: 7.64100
• XLogP3: 7.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 396.339216023
• Heavy Atom Count: 29
• Complexity: 678
• Transport DOT Label: Poison

Purity/Quality:

97% ^*data from raw suppliers

5,6-trans-VitaminD2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Vitamins and Derivatives
• Canonical SMILES: CC(C)C(C)C=CC(C)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C
• Isomeric SMILES: C[C@H](/C=C/[C@H](C)C(C)C)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C\3/C[C@H](CCC3=C)O)C
• Recent EU Clinical Trials: Vitamin D supplementation for prevention of placenta mediated pregnancy complications.
• Uses: 5,6-trans-Vitamin D2 is an isomer as well as one of the main decomposition products of Vitamin D2 (V676040).

Technology Process of 5,6-trans-Vitamin D2

There total 10 articles about 5,6-trans-Vitamin D2 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: 86.0%

(S)-3-[(1R,3aS,7aR)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ6-benzo[c]thiophen-5-ol (87680-65-7) → 3β-hydroxy-9,10-secoergosta-5(E),7(E),10(19),22(E)-tetraene (51744-66-2)

Guidance literature:

With sodium hydrogencarbonate; In methanol; for 2.5h; Heating;

DOI:10.1021/jo00375a013

Reference yield: 58.0%

Calciferol (50-14-6) → 3β-hydroxy-9,10-secoergosta-5(E),7(E),10(19),22(E)-tetraene (51744-66-2)

Guidance literature:

With iodine; In diethyl ether; for 2.5h;

DOI:10.1021/jo00261a020

Reference yield:

ergosta-5,7,22-trien-3β-ol (70005-45-7) → (S)-4-Methylene-3-[2-[(1R,3aS,7aR)-7a-methyl-1-((E)-(R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexanol (50-14-6,51744-66-2,61177-68-2,116559-84-3,137174-35-7) + lumisterol (57-87-4,128-27-8,474-69-1,474-70-4,6538-06-3,7056-23-7,57760-53-9,60018-27-1,70005-45-7,82863-18-1,122565-01-9) + (S)-4-Methyl-3-{(Z)-2-[(1R,3aR,7aR)-7a-methyl-1-((E)-(R)-1,4,5-trimethyl-hex-2-enyl)-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]-vinyl}-cyclohex-3-enol (115-61-7,21307-05-1,24945-48-0,137174-34-6) + tachysterol (115-61-7,21307-05-1,24945-48-0,137174-34-6)

Guidance literature:

In n-heptane; at 25 ℃; Product distribution; Quantum yield; Irradiation;

DOI:10.1007/BF00767270

upstream raw materials:

Calciferol

diethyl ether

(5E)-10-Oxo-19-norergocalciferol

Methylenetriphenylphosphorane

Downstream raw materials:

Calciferol

(3S,5E,7E)-3-(4-phenylazo-benzoyloxy)-9,10-seco-ergosta-5,7,10⁽¹⁹⁾22t-tetraene

toxisterol₂ I₂

toxisterol₂ I₃

Refernces

An allylic nucleophilic substitution reaction of 1 α-hydroxyvitamin D derivatives

10.1016/S0040-4039(00)85093-5

The research focuses on the chemical transformation of 5,6-trans-vitamin D conjugated triene system into that of isovitamin D under nucleophilic conditions. The study reports the first instance of this conversion, which involves a carbanionic intermediate produced by n-butyl-lithium. The reaction is characterized as a novel SN2' reaction where a trialkylsilyloxide anion is substituted by a 1-butyl anion. The purpose of the research was to explore the chemical and biological interest in the transformations of vitamin D derivatives, specifically the conversion of 5,6-e-vitamin D (2) into isovitamin D (3). The key chemicals used in this process include 1,2-dimethylbutyl-lithium (n-butyl-lithium), tetrahydrofuran (THF) as a solvent, and bis-m-butyldimethylsilyl (TBDMS) ether as a protecting group for the la-hydroxy group of vitamin D. The conclusion of the research is that the reaction constitutes a successful conversion of the 5,6-trans-vitamin D triene system into that of isovitamin D under nucleophilic conditions, involving the addition of butyl anion at C-1 to give a pentadienyl carbanion, followed by expulsion of the silyloxide. The study also notes that methyl-lithium reacts similarly and that further exploration of the reaction with other types of nucleophiles is underway.

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