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

Base Information

• Chemical Name: (6R)-SO₂ adduct of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5,7(E),10⁽¹⁹⁾-triene
• CAS No.: 112790-51-9
• Molecular Formula: C₃₄H₆₀O₅SSi₂
• Molecular Weight: 637.084
• Mol file: 112790-51-9.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 13 articles about (6R)-SO₂ adduct of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5,7(E),10⁽¹⁹⁾-triene 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:

(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) → (6R)-SO2 adduct of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5,7(E),10(19)-triene (112790-51-9,266686-81-1) + (6S)-SO2 adduct of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5,7(E),10(19)-triene (112670-80-1,266686-81-1)

Guidance literature:

With ozone; triphenylphosphine; Multistep reaction; 1) CH₂Cl₂, MeOH, -10 deg C, 40 min, 2) room temperature, 3 h;

DOI:10.1021/jo00058a034

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) → (6R)-SO2 adduct of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5,7(E),10(19)-triene (112790-51-9,266686-81-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 63.8 g / SO₂ / CH₂Cl₂ / 0.75 h / -10 °C

2: 1) O₃, 2) Ph₃P / 1) CH₂Cl₂, MeOH, -10 deg C, 40 min, 2) room temperature, 3 h

With sulfur dioxide; ozone; triphenylphosphine; In 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) → (6R)-SO2 adduct of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5,7(E),10(19)-triene (112790-51-9,266686-81-1)

Guidance literature:

Multi-step reaction with 6 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

6: 1) O₃, 2) Ph₃P / 1) CH₂Cl₂, MeOH, -10 deg C, 40 min, 2) room temperature, 3 h

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

DOI:10.1021/jo00058a034

upstream raw materials:

(1S,3R,6R)-bis(tert-butyldimethylsilyloxy)-9,10-seco-ergosta-5,7(E),10⁽¹⁹⁾,22(E)-tetraene SO₂ adduct

(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

Calciferol

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

Downstream raw materials:

(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

1(S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(R)-formyl-9,10-secopregna-5(E),7(E),10(19)-triene

Refernces

• 1、 Guo, Wei,Fang, Zhijie,Li, Hongliang,Liu, Yanan. "Synthesis of 24(28)-methylene-1α-hydroxyvitamin D3, a novel vitamin D3 analogue". . p. 231 - 235. Retrieved 2014/05/06.
• 2、 Calverley. "Synthesis of MC 903, a biologically active vitamin D metabolite analogue". . p. 4609 - 4619,4609-4619. Retrieved 2007/10/02.