ethyl (6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-dihydroxyoctanoate

Base Information

• Chemical Name: ethyl (6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-dihydroxyoctanoate
• CAS No.: 1312759-12-8
• Molecular Formula: C₂₆H₃₈O₅Si
• Molecular Weight: 458.67
• Mol file: 1312759-12-8.mol

Synonyms:ethyl (6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-dihydroxyoctanoate

Chemical Property of ethyl (6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-dihydroxyoctanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-dihydroxyoctanoate

There total 7 articles about ethyl (6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-dihydroxyoctanoate 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: 81.0%

ethyl (6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-(cyclohexylidenedioxy)octanoate (1312759-11-7) → ethyl (6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-dihydroxyoctanoate (1312759-12-8)

Guidance literature:

With water; trifluoroacetic acid; In dichloromethane; at 0 - 25 ℃; for 27h;

DOI:10.1016/j.tetasy.2011.02.008

Reference yield:

(4S,5R)-4-tert-butyldiphenylsilyloxy-5,6-(cyclohexylidenedioxy)hexan-1-ol (1312759-08-2) → ethyl (6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-dihydroxyoctanoate (1312759-12-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium acetate; pyridinium chlorochromate / dichloromethane / 3 h / 0 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 0.25 h / Inert atmosphere

2.2: 18 h / 0 - 25 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen / ethanol / 22 h / 25 °C

4.1: water; trifluoroacetic acid / dichloromethane / 27 h / 0 - 25 °C

With palladium 10% on activated carbon; water; hydrogen; sodium acetate; sodium hydride; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; 2.1: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.tetasy.2011.02.008

Reference yield:

ethyl (2E,6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-(cyclohexylidenedioxy)octenoate (1312759-10-6) → ethyl (6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-dihydroxyoctanoate (1312759-12-8)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen / ethanol / 22 h / 25 °C

2: water; trifluoroacetic acid / dichloromethane / 27 h / 0 - 25 °C

With palladium 10% on activated carbon; water; hydrogen; trifluoroacetic acid; In ethanol; dichloromethane;

DOI:10.1016/j.tetasy.2011.02.008

upstream raw materials:

(2R,3S)-3-tert-butyldiphenylsilyloxy-1,2-(cyclohexylidenedioxy)hex-5-ene

(4S,5R)-4-tert-butyldiphenylsilyloxy-5,6-(cyclohexylidenedioxy)hexan-1-ol

(4S,5R)-4-tert-butyldiphenylsilyloxy-5,6-(cyclohexylidenedioxy)hexanal

ethyl (2E,6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-(cyclohexylidenedioxy)octenoate

Downstream raw materials:

ethyl (6S)-6-tert-butyldiphenylsilyloxyoct-7-enoate

ethyl (6S,7E,9R,10S)-6,10-di-tert-butyldiphenylsilyloxy-9-hydroxyoctadecenoate

C₄₀H₅₀O₉S₂Si

Refernces