(3S)-1,3-Bis-O-tert-ButyldiMethylsilyl 3-Hydroxy VitaMin D2 SO2 Adduct (Mixture of DiastereoMers)

Base Information

• Chemical Name: (3S)-1,3-Bis-O-tert-ButyldiMethylsilyl 3-Hydroxy VitaMin D2 SO2 Adduct (Mixture of DiastereoMers)
• CAS No.: 170081-46-6
• Molecular Formula: C₄₀H₇₂O₄SSi₂
• Molecular Weight: 705.246
• Mol file: 170081-46-6.mol

Synonyms:(6S)- and (6R)-SO₂ adducts of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-9,10-secoergosta-5(E),7(E),10⁽¹⁹⁾,22(E)-tetraene

Chemical Property of (3S)-1,3-Bis-O-tert-ButyldiMethylsilyl 3-Hydroxy VitaMin D2 SO2 Adduct (Mixture of DiastereoMers)

Chemical Property:

• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate

Purity/Quality:

(3S)-1,3-Bis-O-tert-Butyldimethylsilyl3-HydroxyVitaminD2SO2Adduct(MixtureofDiastereomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Intermediate in the preparation of (5E)-Calcipotriene (C144210).

Technology Process of (3S)-1,3-Bis-O-tert-ButyldiMethylsilyl 3-Hydroxy VitaMin D2 SO2 Adduct (Mixture of DiastereoMers)

There total 8 articles about (3S)-1,3-Bis-O-tert-ButyldiMethylsilyl 3-Hydroxy VitaMin D2 SO2 Adduct (Mixture of DiastereoMers) 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:

1(S),3(R)-bis(tert-butyldimethylsilyloxy)-9,10-secoergosta-5(E),7(E),10(19),22(E)-tetraene (115540-28-8,125136-23-4,111594-58-2,184851-16-9) → (6S)- and (6R)-SO2 adducts of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-9,10-secoergosta-5(E),7(E),10(19),22(E)-tetraene (170081-46-6)

Guidance literature:

With sulfur dioxide; In dichloromethane; at -10 ℃; for 0.75h;

DOI:10.1021/jo00058a034

Reference yield:

Calciferol (50-14-6) → (6S)- and (6R)-SO2 adducts of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-9,10-secoergosta-5(E),7(E),10(19),22(E)-tetraene (170081-46-6)

Guidance literature:

Multi-step reaction with 6 steps

1: SO₂ / CH₂Cl₂ / 1.25 h / -10 °C

2: imidazole / Ambient temperature

3: 94 percent / NaHCO₃ / aq. ethanol / 1.25 h / Heating

4: 54.9 g / SeO₂, 4-methylmorpholine N-oxide / methanol / 5.5 h / Heating

5: imidazole / CH₂Cl₂ / 6 h / Ambient temperature

6: 63.8 g / SO₂ / CH₂Cl₂ / 0.75 h / -10 °C

With 1H-imidazole; selenium(IV) oxide; sulfur dioxide; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; In methanol; ethanol; dichloromethane;

DOI:10.1021/jo00058a034

Reference yield:

(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) → (6S)- and (6R)-SO2 adducts of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-9,10-secoergosta-5(E),7(E),10(19),22(E)-tetraene (170081-46-6)

Guidance literature:

Multi-step reaction with 5 steps

1: imidazole / Ambient temperature

2: 94 percent / NaHCO₃ / aq. ethanol / 1.25 h / Heating

3: 54.9 g / SeO₂, 4-methylmorpholine N-oxide / methanol / 5.5 h / Heating

4: imidazole / CH₂Cl₂ / 6 h / Ambient temperature

5: 63.8 g / SO₂ / CH₂Cl₂ / 0.75 h / -10 °C

With 1H-imidazole; selenium(IV) oxide; sulfur dioxide; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; In methanol; ethanol; dichloromethane;

DOI:10.1021/jo00058a034

upstream raw materials:

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

Calciferol

(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)-3-(tert-butyldimethylsilyl)-9,10-secoergosta-5(E),7(E),10⁽¹⁹⁾,22(E)-tetraene-1-ol

Downstream raw materials:

1alpha,24(S)-Dihydroxyvitamin D₃

tacalcitol

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

(5E,7E)-(1S,3R,20S)-1,3-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-20-methyl-9,10-secopregna-5,7,10(19)-trien-21-al