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

Base Information

• Chemical Name: (1S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-3-[2-[(1R,3aS)-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-cyclohexanol
• CAS No.: 112670-78-7
• Molecular Formula: C₃₄H₅₈O₂Si
• Molecular Weight: 526.919
• Mol file: 112670-78-7.mol

Synonyms:

Chemical Property of (1S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-3-[2-[(1R,3aS)-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-cyclohexanol

Chemical Property:

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-3-[2-[(1R,3aS)-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-cyclohexanol

There total 25 articles about (1S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-3-[2-[(1R,3aS)-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-cyclohexanol 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:

(5E)-vitamin D2 tert-butyldimethylsilyl ether (104846-62-0,104846-63-1) → 1(S),3(R)-3-(tert-butyldimethylsilyl)-9,10-secoergosta-5(E),7(E),10(19),22(E)-tetraene-1-ol + 1(S),3(R)-3-(tert-butyldimethylsilyl)-9,10-secoergosta-5(E),7(E),10(19),22(E)-tetraene-1-ol (115540-27-7,132152-22-8,112670-78-7)

Guidance literature:

With selenium(IV) oxide; 4-methylmorpholine N-oxide; In methanol; dichloromethane; at 42 ℃; optical yield given as %de; Inert atmosphere; Sonication;

DOI:10.1021/op200346g

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) → 1(S),3(R)-3-(tert-butyldimethylsilyl)-9,10-secoergosta-5(E),7(E),10(19),22(E)-tetraene-1-ol (112670-78-7,115540-27-7,132152-22-8)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/jo00058a034

Reference yield:

(5E)-vitamin D2 tert-butyldimethylsilyl ether (104846-62-0,104846-63-1) → 1(S),3(R)-3-(tert-butyldimethylsilyl)-9,10-secoergosta-5(E),7(E),10(19),22(E)-tetraene-1-ol (112670-78-7,115540-27-7,132152-22-8)

Guidance literature:

With selenium(IV) oxide; 4-methylmorpholine N-oxide; In methanol; dichloromethane; for 0.833333h; Yield given; Heating;

DOI:10.1016/S0040-4020(01)86903-9

upstream raw materials:

Calciferol

tert-butyldimethylsilyl chloride

(5E)-vitamin D₂ tert-butyldimethylsilyl ether

SO2-adduct of 3(S)-<(tert-butyldimethylsilyl)oxy>-9,10-secoergosta-5,7(E),10(19),22(E)-tetraene

Downstream raw materials:

(1R,3aS,7aR)-4-[2-[(3S,5R)-3-(Allyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-indene

(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

(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