(7Z)-Vitamin D₂

Base Information

• Chemical Name: (7Z)-Vitamin D₂
• CAS No.: 247900-07-8
• Molecular Formula: C₂₈H₄₄O
• Molecular Weight: 396.657
• Mol file: 247900-07-8.mol

Synonyms:(7Z)-Vitamin D₂

Chemical Property of (7Z)-Vitamin D₂

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (7Z)-Vitamin D₂

There total 8 articles about (7Z)-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:

tert-Butyl-dimethyl-{(S)-4-methylene-3-[2-[(1R,3aS,7aR)-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexyloxy}-silane → Calciferol (50-14-6) + (7Z)-Vitamin D2 (247900-07-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; overnight;

DOI:10.1055/s-1999-3530

Reference yield:

(4R,7aR)-1-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-4-((R,Z)-1-hydroxy-2-((S)-5-hydroxy-2-methylenecyclohexylidene)ethyl)-7a-methyloctahydro-1H-inden-4-ol (84985-78-4) → (7Z)-Vitamin D2 (247900-07-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 89 percent / imidazole; DMAP / CH₂Cl₂ / 20 °C

2.1: pyridine; Pb(OAc)4 / CH₂Cl₂ / 0.25 h / 0 °C

2.2: 83 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.25 h / 0 °C

3.1: 81 percent / Amberlite<*> IR-118 ion-exchange resin; Na; EtOH / diethyl ether / 2.5 h / 0 °C

4.1: 72 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 25 h / 0 - 20 °C

5.1: 73 percent / H₂O₂ / (NH₄)6Mo₇O₂₄*4H₂O / aq. ethanol / 240 h / 20 °C

6.1: NaHMDS / diethyl ether; tetrahydrofuran / 1 h / -78 °C

6.2: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

6.3: diethyl ether; tetrahydrofuran / -100 - 20 °C

7.1: Bu₄NF*3H₂O / tetrahydrofuran / 20 °C / overnight

With pyridine; 1H-imidazole; lead(IV) acetate; dmap; ethanol; di-isopropyl azodicarboxylate; Amberlite<*> IR-118 ion-exchange resin; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hexamethyldisilazane; sodium; triphenylphosphine; ammonium heptamolybdate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; 1.1: Etherification / 2.1: Oxidation / 2.2: Reduction / 3.1: Reduction / 4.1: Mitsunobu reaction / 5.1: Catalytic oxidation / 6.1: Metallation / 6.2: Dess-Martin oxidation / 6.3: Alkylation / 7.1: desilylation;

DOI:10.1055/s-1999-3530

Reference yield:

(5Z,22E)-(7R)-3β-(tert-butyldimethylsilyloxy)-9,10-seco-8α-ergosta-5,10(19),22-triene-7,8-diol (131852-63-6) → (7Z)-Vitamin D2 (247900-07-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridine; Pb(OAc)4 / CH₂Cl₂ / 0.25 h / 0 °C

1.2: 83 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.25 h / 0 °C

2.1: 81 percent / Amberlite<*> IR-118 ion-exchange resin; Na; EtOH / diethyl ether / 2.5 h / 0 °C

3.1: 72 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 25 h / 0 - 20 °C

4.1: 73 percent / H₂O₂ / (NH₄)6Mo₇O₂₄*4H₂O / aq. ethanol / 240 h / 20 °C

5.1: NaHMDS / diethyl ether; tetrahydrofuran / 1 h / -78 °C

5.2: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

5.3: diethyl ether; tetrahydrofuran / -100 - 20 °C

6.1: Bu₄NF*3H₂O / tetrahydrofuran / 20 °C / overnight

With pyridine; lead(IV) acetate; ethanol; di-isopropyl azodicarboxylate; Amberlite<*> IR-118 ion-exchange resin; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hexamethyldisilazane; sodium; triphenylphosphine; ammonium heptamolybdate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; 1.1: Oxidation / 1.2: Reduction / 2.1: Reduction / 3.1: Mitsunobu reaction / 4.1: Catalytic oxidation / 5.1: Metallation / 5.2: Dess-Martin oxidation / 5.3: Alkylation / 6.1: desilylation;

DOI:10.1055/s-1999-3530

upstream raw materials:

(1R,3aR,7aR)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-one

(2Z)-2-<(5S)-5-(tert-butyldimethylsilyloxy)-2-methylene-cyclohexylidene>-ethanol

(4R,7aR)-1-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-4-((R,Z)-1-hydroxy-2-((S)-5-hydroxy-2-methylenecyclohexylidene)ethyl)-7a-methyloctahydro-1H-inden-4-ol

(5Z,22E)-(7R)-3β-(tert-butyldimethylsilyloxy)-9,10-seco-8α-ergosta-5,10(19),22-triene-7,8-diol

Downstream raw materials:

(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

1(S),3(R)-bis(tert-butyldimethylsilyloxy)-9,10-secoergosta-5(E),7(E),10⁽¹⁹⁾,22(E)-tetraene

(6R)-SO₂ adduct of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5,7(E),10⁽¹⁹⁾-triene

(6S)-SO₂ adduct of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5,7(E),10⁽¹⁹⁾-triene

Refernces