[3S,4R,5R,6S,7R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(tert-butyldiphenylsilyl)oxy]-5,7-dimethyl-3-methoxy-oct-1-ene-4-ol

Base Information

• Chemical Name: [3S,4R,5R,6S,7R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(tert-butyldiphenylsilyl)oxy]-5,7-dimethyl-3-methoxy-oct-1-ene-4-ol
• CAS No.: 443283-75-8
• Molecular Formula: C₃₃H₅₄O₄Si₂
• Molecular Weight: 570.96

Synonyms:[3S,4R,5R,6S,7R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(tert-butyldiphenylsilyl)oxy]-5,7-dimethyl-3-methoxy-oct-1-ene-4-ol

Chemical Property of [3S,4R,5R,6S,7R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(tert-butyldiphenylsilyl)oxy]-5,7-dimethyl-3-methoxy-oct-1-ene-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of [3S,4R,5R,6S,7R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(tert-butyldiphenylsilyl)oxy]-5,7-dimethyl-3-methoxy-oct-1-ene-4-ol

There total 1 articles about [3S,4R,5R,6S,7R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(tert-butyldiphenylsilyl)oxy]-5,7-dimethyl-3-methoxy-oct-1-ene-4-ol 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:

3,3-dimethoxyprop-1-ene (6044-68-4) + (2S,3S,4R)-3-((tert-butyldimethylsilyl)oxy)-5-((tert-butyldiphenylsilyl)oxy)-2,4-dimethylpentanal → [3R,4S,5R,6S,7R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(tert-butyldiphenylsilyl)oxy]-5,7-dimethyl-3-methoxy-oct-2-ene-4-ol (443283-76-9) + [3S,4R,5R,6S,7R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(tert-butyldiphenylsilyl)oxy]-5,7-dimethyl-3-methoxy-oct-1-ene-4-ol (443283-75-8)

Guidance literature:

With chromium dichloride; trimethylsilyl iodide; at -42 ℃;

DOI:10.1021/jo016413f

Reference yield:

[3S,4R,5R,6S,7R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(tert-butyldiphenylsilyl)oxy]-5,7-dimethyl-3-methoxy-oct-1-ene-4-ol (443283-75-8) → (2S,3R,4R,5S,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-2-methoxy-4,6-dimethyl-heptane-1,3-diol

Guidance literature:

[3S,4R,5R,6S,7R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(tert-butyldiphenylsilyl)oxy]-5,7-dimethyl-3-methoxy-oct-1-ene-4-ol; With ozone; In methanol; dichloromethane; at -78 ℃;

With sodium tetrahydroborate; In methanol; dichloromethane; Further stages.;

DOI:10.1021/jo016413f

Reference yield:

[3S,4R,5R,6S,7R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(tert-butyldiphenylsilyl)oxy]-5,7-dimethyl-3-methoxy-oct-1-ene-4-ol (443283-75-8) → [3S,4R,5S,6S,7R]-8-[(tert-butyldiphenylsilyl)oxy]-5,7-dimethyl-4,6-O-isopropylidene-3-methoxy-oct-2-ene-4,6-diol

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / pyridinium p-toluenesulfonate / ethanol / 24 h / 55 °C

2: 53 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 0.25 h

With pyridinium p-toluenesulfonate; In ethanol; dichloromethane;

DOI:10.1021/jo016413f

upstream raw materials:

3,3-dimethoxyprop-1-ene

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