Cyclooctanone, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-8-(hydroxymethyl)-5-[(4-methoxy phenyl)methoxy]-4,4-dimethyl-7-[1-methylene-4-[(triethylsilyl)oxy]butyl]-2, 6-bis(phenylmethoxy)-, (2R,3R,5R,6S,7S,8R)-

Base Information

• Chemical Name: Cyclooctanone, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-8-(hydroxymethyl)-5-[(4-methoxy phenyl)methoxy]-4,4-dimethyl-7-[1-methylene-4-[(triethylsilyl)oxy]butyl]-2, 6-bis(phenylmethoxy)-, (2R,3R,5R,6S,7S,8R)-
• CAS No.: 553628-46-9
• Molecular Formula: C50H76O8Si2
• Molecular Weight: 861.32

Synonyms:

Chemical Property of Cyclooctanone, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-8-(hydroxymethyl)-5-[(4-methoxy phenyl)methoxy]-4,4-dimethyl-7-[1-methylene-4-[(triethylsilyl)oxy]butyl]-2, 6-bis(phenylmethoxy)-, (2R,3R,5R,6S,7S,8R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cyclooctanone, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-8-(hydroxymethyl)-5-[(4-methoxy phenyl)methoxy]-4,4-dimethyl-7-[1-methylene-4-[(triethylsilyl)oxy]butyl]-2, 6-bis(phenylmethoxy)-, (2R,3R,5R,6S,7S,8R)-

There total 2 articles about Cyclooctanone, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-8-(hydroxymethyl)-5-[(4-methoxy phenyl)methoxy]-4,4-dimethyl-7-[1-methylene-4-[(triethylsilyl)oxy]butyl]-2, 6-bis(phenylmethoxy)-, (2R,3R,5R,6S,7S,8R)- 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: 71.0%

2-bromo-5-(triethylsilyloxy)pentene (178626-24-9) + (4S,5R,7R,8R)-4,8-bis(benzyloxy)-7-(t-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-6,6-dimethylcyclooct-2-enone → (2R,3R,5R,6S,7R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-4,4-dimethyl-8-methylene-7-[1-methylene-4-(triethylsilyloxy)butyl]cyclooctanone (553628-47-0) + (2R,3R,5R,6S,7S,8R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsilyloxy)-8-hydroxymethyl-5-(4-methoxybenzyloxy)-4,4-dimethyl-7-[1-methylene-4-(triethylsilyloxy)butyl]cyclooctanone (553628-46-9)

Guidance literature:

(4S,5R,7R,8R)-4,8-bis(benzyloxy)-7-(t-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-6,6-dimethylcyclooct-2-enone; With trimethylaluminum; In diethyl ether; hexane; at 0 ℃; for 0.5h;

2-bromo-5-(triethylsilyloxy)pentene; With tert.-butyl lithium; In diethyl ether; hexane; pentane; at -23 ℃; for 1h;

With ammonium chloride; In diethyl ether; hexane; pentane; at -78 ℃;

Reference yield:

(2S,3R,5R,6R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxo-8-(triethylsilyloxymethyl)cyclooctyl acetate → (2R,3R,5R,6S,7S,8R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsilyloxy)-8-hydroxymethyl-5-(4-methoxybenzyloxy)-4,4-dimethyl-7-[1-methylene-4-(triethylsilyloxy)butyl]cyclooctanone (553628-46-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 26 percent / DBU / benzene / 0.5 h / 20 °C

2.1: t-butyllithium / diethyl ether / 0.5 h / -78 °C

2.2: CuCN / diethyl ether / 0.33 h / -23 °C

2.3: 71 percent / trimethylaluminium / diethyl ether; hexane / 1 h / -23 °C

With tert.-butyl lithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; In diethyl ether; benzene;

DOI:10.1246/bcsj.78.677

Reference yield: 89.0%

acetic anhydride (108-24-7) + (2R,3R,5R,6S,7S,8R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsilyloxy)-8-hydroxymethyl-5-(4-methoxybenzyloxy)-4,4-dimethyl-7-[1-methylene-4-(triethylsilyloxy)butyl]cyclooctanone (553628-46-9) → (1R,3R,4R,6R,7S,8R)-3,7-bis(benzyloxy)-4-(t-butyldimethylsilyloxy)-6-(methoxybenzyloxy)-5,5-dimethyl-8-[1-methylene-4-(triethylsilyloxy)butyl]cyclooctylmethyl acetate (677751-20-1)

Guidance literature:

With dmap; In pyridine;

DOI:10.1246/cl.2004.124

upstream raw materials:

2-bromo-5-(triethylsilyloxy)pentene

Downstream raw materials:

(1R,3R,4R,6R,7S,8R)-3,7-bis(benzyloxy)-4-(t-butyldimethylsilyloxy)-6-(methoxybenzyloxy)-5,5-dimethyl-8-[1-methylene-4-(triethylsilyloxy)butyl]cyclooctylmethyl acetate

(2R,3R,5R,6S,7R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-4,4-dimethyl-8-methylene-7-[1-methylene-4-(triethylsilyloxy)butyl]cyclooctanone

(2R,3R,5R,6S,7R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsilyloxy)-7-(4-hydroxy-1-methylenebutyl)-5-(4-methoxybenzyloxy)-4,4-dimethyl-8-methylenecyclooctanone

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