(5S,6S,7R)-(E)-1-(tert-butyldiphenylsilyloxy)-6,8-dihydroxy-5,7-dimethyl-3-octene

Base Information

• Chemical Name: (5S,6S,7R)-(E)-1-(tert-butyldiphenylsilyloxy)-6,8-dihydroxy-5,7-dimethyl-3-octene
• CAS No.: 313696-87-6
• Molecular Formula: C₂₆H₃₈O₃Si
• Molecular Weight: 426.671
• Mol file: 313696-87-6.mol

Synonyms:(5S,6S,7R)-(E)-1-(tert-butyldiphenylsilyloxy)-6,8-dihydroxy-5,7-dimethyl-3-octene

Chemical Property of (5S,6S,7R)-(E)-1-(tert-butyldiphenylsilyloxy)-6,8-dihydroxy-5,7-dimethyl-3-octene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6S,7R)-(E)-1-(tert-butyldiphenylsilyloxy)-6,8-dihydroxy-5,7-dimethyl-3-octene

There total 2 articles about (5S,6S,7R)-(E)-1-(tert-butyldiphenylsilyloxy)-6,8-dihydroxy-5,7-dimethyl-3-octene 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: 90.0%

(5S,6S,7R)-(E)-8-benzyloxy-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-5,7-dimethyl-3-octene (313696-86-5) → (5S,6S,7R)-(E)-1-(tert-butyldiphenylsilyloxy)-6,8-dihydroxy-5,7-dimethyl-3-octene (313696-87-6)

Guidance literature:

With boron trichloride; In hexane; toluene; at -78 ℃; for 5h;

DOI:10.1021/ja002377a

Reference yield:

(4S)-(E)-6-(tert-butyldiphenylsilyloxy)-4-(dimethylphenyl)silyl-2-hexene → (5S,6S,7R)-(E)-1-(tert-butyldiphenylsilyloxy)-6,8-dihydroxy-5,7-dimethyl-3-octene (313696-87-6)

Guidance literature:

Multi-step reaction with 2 steps

1: TiCl₄ / CH₂Cl₂ / 5 h / -78 °C

2: 90 percent / boron trichloride / toluene; hexane / 5 h / -78 °C

With boron trichloride; titanium tetrachloride; In hexane; dichloromethane; toluene;

DOI:10.1021/ja002377a

Reference yield: 89.0%

4-methoxy-benzaldehyde (123-11-5) + (5S,6S,7R)-(E)-1-(tert-butyldiphenylsilyloxy)-6,8-dihydroxy-5,7-dimethyl-3-octene (313696-87-6) → (5S,6S,7R)-(E)-1-(tert-butyldiphenylsilyloxy)-6,8-(para-methoxybenzylidene)dioxy-5,7-dimethyl-3-octene (313696-88-7)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; at 25 ℃; for 20h;

DOI:10.1021/ja002377a

upstream raw materials:

(5S,6S,7R)-(E)-8-benzyloxy-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-5,7-dimethyl-3-octene

Downstream raw materials:

(5S,6S,7R)-(E)-1-(tert-butyldiphenylsilyloxy)-6,8-(para-methoxybenzylidene)dioxy-5,7-dimethyl-3-octene

(3R,4R,5R,9S,10S,12S,13R,14S)-12-(tert-butyldimethylsilyloxy)-10,14-dimethoxy-4-(para-methoxybenzyloxy)-3,5,9,13-tetramethyl-6,16-dioxo-1-hexadecanal 2,2-dimethyl-1,3-propanediol acetal

C₆₆H₈₉N₃O₁₅Si

9-{2''-[14-acetoxy-16-(5,5-dimethyl-[1,3]dioxan-2-yl)-6-hydroxy-4,8-dimethoxy-5,9,13,15-tetramethyl-12-oxo-hexadec-1-enyl]-[2,4';2',4'']teroxazol-4-yl}-3-(tert-butyl-diphenyl-silanyloxy)-9-methoxy-8-methyl-7-oxo-non-5-enoic acid