8β-tert-butyldimethylsilyloxy-(17E)-[1-(3-bromophenyl)methylidene]-de-A,B-androstane

Base Information

• Chemical Name: 8β-tert-butyldimethylsilyloxy-(17E)-[1-(3-bromophenyl)methylidene]-de-A,B-androstane
• CAS No.: 282724-83-8
• Molecular Formula: C₂₃H₃₅BrOSi
• Molecular Weight: 435.52
• Mol file: 282724-83-8.mol

Synonyms:8β-tert-butyldimethylsilyloxy-(17E)-[1-(3-bromophenyl)methylidene]-de-A,B-androstane

Chemical Property of 8β-tert-butyldimethylsilyloxy-(17E)-[1-(3-bromophenyl)methylidene]-de-A,B-androstane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8β-tert-butyldimethylsilyloxy-(17E)-[1-(3-bromophenyl)methylidene]-de-A,B-androstane

There total 1 articles about 8β-tert-butyldimethylsilyloxy-(17E)-[1-(3-bromophenyl)methylidene]-de-A,B-androstane 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: 12.0%

P-[(3-bromophenyl)methyl]phosphonic acid diethyl ester (128833-03-4) + 8β-[(tert-butyldimethylsilyl)oxy]de-A,B-androstan-17β-one (140659-26-3) → 8β-tert-butyldimethylsilyloxy-(17Z)-[1-(3-bromophenyl)methylidene]-de-A,B-androstane + 8β-tert-butyldimethylsilyloxy-(17E)-[1-(3-bromophenyl)methylidene]-de-A,B-androstane (282724-83-8)

Guidance literature:

With potassium hydride; In tetrahydrofuran; for 4h; Heating;

DOI:10.1021/jo000579j

Reference yield: 86.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + 8β-tert-butyldimethylsilyloxy-(17E)-[1-(3-bromophenyl)methylidene]-de-A,B-androstane (282724-83-8) → 8β-tert-butyldimethylsilyloxy-(17E)-{1-[3-(methyloxycarbonyl)phenyl]methylidene}-de-A,B-androstane (282724-94-1)

Guidance literature:

With 1,3-bis-(diphenylphosphino)propane; triethylamine; palladium diacetate; In dimethyl sulfoxide; at 80 ℃; for 12h;

DOI:10.1021/jo000579j

Reference yield:

8β-tert-butyldimethylsilyloxy-(17E)-[1-(3-bromophenyl)methylidene]-de-A,B-androstane (282724-83-8) → (17Z)-{1-[3-(methyloxycarbonyl)phenyl]methylidene}-de-A,B-androstan-8-one (307318-49-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / Et₃N; dppp / Pd(OAc)2 / dimethylsulfoxide / 12 h / 80 °C

2: 75 percent / tetrahydrofuran / 1.5 h / Irradiation

3: 94 percent / aq. HF / acetonitrile / 3 h / 20 °C

4: 97 percent / PDC / CH₂Cl₂ / 8 h

With dipyridinium dichromate; 1,3-bis-(diphenylphosphino)propane; hydrogen fluoride; triethylamine; palladium diacetate; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; acetonitrile; 1: Addition / 2: Isomerization / 3: Decomposition / 4: Oxidation;

DOI:10.1021/jo000579j

upstream raw materials:

P-[(3-bromophenyl)methyl]phosphonic acid diethyl ester

8β-[(tert-butyldimethylsilyl)oxy]de-A,B-androstan-17β-one

Downstream raw materials:

8β-tert-butyldimethylsilyloxy-(17E)-{1-[3-(methyloxycarbonyl)phenyl]methylidene}-de-A,B-androstane

(17Z)-{1-[3-(methyloxycarbonyl)phenyl]methylidene}-de-A,B-androstan-8-one

(17E)-{1-[3-(methyloxycarbonyl)phenyl]methylidene}-de-A,B-androstan-8-one

(17Z)-{1-[3-(methyloxycarbonyl)phenyl]methylidene}-de-A,B-androstan-8β-ol